Synthesis 2016; 48(22): 3890-3906
DOI: 10.1055/s-0035-1562793
short review
© Georg Thieme Verlag Stuttgart · New York

The Diamino Analogues of Privileged Corey–Bakshi–Shibata and Jørgensen–Hayashi Catalysts: A Comparison of Their Performance

Jorge Vargas-Caporali*
a  Departamento de Química, Centro de Investigación y de Estudios Avanzados, Instituto Politécnico Nacional, Avenida IPN No. 2508, 07360 Ciudad de México, México   Email: [email protected]   Email: [email protected]
,
Eusebio Juaristi*
a  Departamento de Química, Centro de Investigación y de Estudios Avanzados, Instituto Politécnico Nacional, Avenida IPN No. 2508, 07360 Ciudad de México, México   Email: [email protected]   Email: [email protected]
b  El Colegio Nacional, Luis González Obregón No. 23, Centro Histórico, 06020 Ciudad de México, México
› Author Affiliations
Further Information

Publication History

Received: 28 June 2016

Accepted: 29 June 2016

Publication Date:
01 September 2016 (online)


Abstract

α,α-Diarylprolinol derivatives are well-established families of organocatalysts that are widely used to promote diverse asymmetric reactions. The enantioinduction generated from these ligands is mainly due to the gem-diphenyl carbinol fragment. For this reason, the synthesis of diaza analogues seemed an evident and attractive issue to address in the development of alternative chiral ligands. Although the O→N substitution and subsequent derivatization at first glance looked simple, it was necessary to deal with various unexpected synthetic difficulties. It was established that suitable modifications of the side chain in the diaza analogues afford reaction yields and stereoselectivities that are comparable to those exhibited by the amino alcohol analogues. Nevertheless, various potential applications still remain undeveloped.

1 Introduction

2 Oxazaborolidines and Diazaborolidines in Borane-Mediated Reduction of Prochiral Ketones

3 Organocatalyzed Asymmetric Epoxidations

4 Assessing the Organocatalytic Capability of the α,α-Diphenylprolinol Diaza-Analogues through Benchmark Mannich and Michael Reactions

 
  • References

  • 1 Kapfhammer J, Matthes A. Z. Physiol. Chem. 1934; 223: 43
    • 2a Soai K, Ookawa A, Ogawa K, Kaba T. J. Chem. Soc., Chem. Commun. 1987; 467
    • 2b Soai K, Ookawa A, Kaba T, Ogawa K. J. Am. Chem. Soc. 1987; 109: 7111
    • 3a Enders D, Eichenauer H. Tetrahedron Lett. 1977; 18: 191

    • For more recent reports, see:
    • 3b Enders D, Dhulut S, Steinbusch D, Herrbach A. Chem. Eur. J. 2007; 13: 3942
    • 3c Brehme R, Enders D, Fernandez R, Lassaletta JM. Eur. J. Org. Chem. 2007; 5629
  • 4 Enders D, Kipphardt H, Gerdes P, Breña-Valle L, Bhushan V. Bull. Soc. Chim. Belg. 1988; 97: 691
  • 5 Enders D, Bhushan V. Tetrahedron Lett. 1988; 29: 2437
    • 6a Hirao A, Itsuno S, Nakahama S, Yamazaki N. J. Chem. Soc., Chem. Commun. 1981; 315
    • 6b Itsuno S, Ito K, Hirao A, Nakahama S. J. Chem. Soc., Chem. Commun. 1983; 469
    • 6c Itsuno S, Hirao A, Nakahama S, Yamazaki N. J. Chem. Soc., Perkin Trans. 1 1983; 1673
    • 6d Itsuno S, Ito K, Hirao A, Nakahama S. J. Org. Chem. 1984; 49: 555
    • 6e Itsuno S, Nakano M, Miyazaki K, Masuda H, Ito K, Hirao A, Nakahama S. J. Chem. Soc., Perkin Trans. 1 1985; 2039
    • 6f Itsuno S, Sarukai Y, Ito K, Hirao A, Nakahama S. Bull. Chem. Soc. Jpn. 1987; 60: 395
  • 7 Corey EJ, Bakshi RK, Shibata S. J. Am. Chem. Soc. 1987; 109: 5551
    • 8a Mathre DJ, Thomson AS, Douglas AW, Hoogsteen K, Carroll JD, Corley EG, Grabowski EJ. J. J. Org. Chem. 1993; 58: 2880
    • 8b Salunkhe AM, Burkhardt ER. Tetrahedron Lett. 1997; 38: 1523
    • 8c Ortiz-Maciales M, De Jesús M, González E, Raptis RG, Baran P. Acta Crystallogr. 2004; C60: o173
    • 9a Corey EJ, Bakshi RK, Shibata S, Chen C.-P, Singh VK. J. Am. Chem. Soc. 1987; 109: 7925
    • 9b Corey EJ, Azimiora M, Sarshar S. Tetrahedron Lett. 1992; 33: 3429
    • 9c Mathre DJ, Jones TK, Xavier LC, Blacklock TJ, Reamer RA, Mohan JJ, Turne Jones ET, Hoogsteen K, Baum MW, Grabowski EJ. J. J. Org. Chem. 1991; 56: 751
    • 10a Jones DK, Liotta DC. J. Org. Chem. 1993; 58: 799
    • 10b Alagona G, Ghio C, Persico M, Tomasi S. J. Am. Chem. Soc. 2003; 125: 10027
    • 10c Alagona G, Ghio C, Tomasi S. Theor. Chem. Acc. 2004; 111: 287

      For excellent reviews regarding enantioselective reduction of ketones with chiral oxazaborolidines employed as catalysts, and mechanistic considerations, see:
    • 12a Corey E, Helal CJ. Angew. Chem. Int. Ed. 1998; 37: 1986
    • 12b Wallbaum S, Martens J. Tetrahedron: Asymmetry 1992; 3: 1475
    • 12c Itsuno S In Comprehensive Asymmetric Catalysis . Vol. I. Jacobsen EN, Pfaltz A, Yamamoto H. Springer Verlag; Berlin: 2000: 351
  • 13 Willems JG. H, Dommerholt FJ, Hammink JB, Vaarhorst AM, Thijs L, Zwaneburg B. Tetrahedron Lett. 1995; 36: 603
    • 14a Rama Rao AV, Gurjar MK, Kaiwar V. Tetrahedron: Asymmetry 1992; 3: 859
    • 14b Behnen W, Dauelsberg C, Wallbaum J, Martens J. Synth. Commun. 1992; 22: 2143
  • 15 Rama Rao AV, Gurjar MK, Sharma PA, Kaiwar V. Tetrahedron Lett. 1990; 31: 2341
    • 16a Kim YH, Park DH, Byun IS, Yoon IK, Park CS. J. Org. Chem. 1993; 58: 4511
    • 16b Martens J, Dauelsberg C, Behnen W, Wallbaum S. Tetrahedron: Asymmetry 1992; 3: 347
  • 17 Corey EJ, Link JO. Tetrahedron Lett. 1989; 30: 6275
  • 18 Demir AS, Mecitoglu E, Tanyeli C, Gülbeyaz V. Tetrahedron: Asymmetry 1996; 7: 3359
  • 19 Corey EJ, Link JO. Tetrahedron Lett. 1990; 31: 601
  • 20 Helal CJ, Magriotis PA, Corey EJ. J. Am. Chem. Soc. 1996; 118: 10938
    • 21a Cho BT, Chun YS. J. Chem. Soc., Perkin Trans. 1 1999; 2095
    • 21b Mahale RD, Chaskar SP, Patil KE, Maipak GC, Gurjar MK. Org. Process Res. Dev. 2012; 16: 710
    • 22a Corey EJ, Link JO. Tetrahedron Lett. 1992; 33: 3431
    • 22b Corey EJ, Bakshi RK. Tetrahedron Lett. 1990; 31: 611
  • 23 Chen C.-P, Prasad K, Repic O. Tetrahedron Lett. 1991; 32: 7175
  • 24 Corey EJ, Helal CJ. Tetrahedron Lett. 1996; 37: 5675
    • 25a Nicolaou KC, Bertinato P, Piscopio AD, Chakraborty TK, Minowa N. J. Chem. Soc., Chem. Commun. 1993; 619
    • 25b Ikoma A, Kobayashi Y. Synlett 2014; 25: 1150
    • 26a Simpson AF, Szeto P, Lathbury DC, Gallagher T. Tetrahedron: Asymmetry 1997; 8: 673
    • 26b Simpson AF, Bodkin CD, Butts CP, Armitage MA, Gallagher T. J. Chem. Soc., Perkin Trans. 1 2000; 3047
  • 27 Corey EJ, Helal CJ. Tetrahedron Lett. 1995; 36: 9153
  • 28 Corey EJ, Guzman-Perez A, Lazerwith SE. J. Am. Chem. Soc. 1997; 119: 11769
    • 29a Amigoni SJ, Toupet LJ, Le Floc’h YJ. J. Org. Chem. 1997; 62: 6374
    • 29b Dumartin H, Le Floc’h Y, Grée R. Tetrahedron Lett. 1994; 35: 6681
  • 30 Parker KA, Ledeboer MW. J. Org. Chem. 1996; 61: 3214
  • 31 Corey EJ, Cheng X.-M, Cimprich KA, Sarshar S. Tetrahedron Lett. 1991; 32: 6835
  • 32 DeNinno MP, Perner RP, Lijewski L. Tetrahedron Lett. 1990; 31: 7415
  • 33 Corey EJ, Link JO. J. Am. Chem. Soc. 1992; 114: 1906
  • 34 Khrimian AP, Oliver JE, Waters RM, Panicker S, Nicholson JM, Klun JA. Tetrahedron: Asymmetry 1996; 7: 37
  • 35 Corey EJ, Helal CJ. Tetrahedron Lett. 1993; 34: 5227
    • 36a Denopamine: Corey EJ, Link JO. J. Org. Chem. 1991; 56: 442
    • 36b Isoproterenol: see ref 19.
  • 37 Corey EJ, Reichard GA. Tetrahedron Lett. 1989; 30: 5207
    • 38a Brunel J.-M, Pardigon O, Faure B, Buono G. J. Chem. Soc., Chem. Commun. 1992; 287
    • 38b Brunel J.-M, Chiodi O, Faure B, Fotiadu F, Buono G. J. Organomet. Chem. 1997; 529: 285
    • 38c Burns B, King NP, Studley JR, Tye H, Wills M. Tetrahedron: Asymmetry 1994; 5: 801
  • 39 Froelich O, Bonin M, Quirion J.-C, Husson H.-P. Tetrahedron: Asymmetry 1993; 4: 2335
    • 40a Asami M, Sato S, Watanabe H. Chem. Lett. 2000; 990
    • 40b Sato S, Watanabe H, Asami M. Tetrahedron: Asymmetry 2000; 11: 4329
    • 41a Asami M, Ohno H, Kobayashi S, Mukaiyama T. Bull. Chem. Soc. Jpn. 1978; 51: 1869
    • 41b Asami M. Bull. Chem. Soc. Jpn. 1990; 63: 721
    • 41c Asami M, Usui K, Higuchi S, Inoue S. Chem. Lett. 1994; 297
    • 41d Asami M, Ishizaki T, Inoue S. Tetrahedron: Asymmetry 1994; 5: 793
    • 41e Asami M, Inoue S. Bull. Chem. Soc. Jpn. 1997; 70: 1687
    • 41f Asami M, Sato S, Honda K, Inoue S. Heterocycles 2000; 52: 1029
  • 42 Asami M, Watanabe H, Honda K, Inoue S. Tetrahedron: Asymmetry 1998; 9: 4165
  • 43 Basavaiah D, Venkateswara Rao K, Sekhara Reddy B. Tetrahedron: Asymmetry 2006; 17: 1041
  • 44 Basavaiah D, Venkateswara Rao K, Sekhara Reddy B. Tetrahedron: Asymmetry 2007; 18: 968
  • 45 Olivares-Romero JL, Juaristi E. Tetrahedron 2008; 64: 9992

    • Also in 2008, Ooi and co-workers described the preparation of several chiral diamines derived from l-valine, l-isoleucine, and l-tert-leucine via azidation of the corresponding diarylamino alcohols:
    • 46a Uraguchi D, Sakaki S, Ueki Y, Ito T, Ooi T. Heterocycles 2008; 76: 1081

    • Furthermore, some years later Lee and co-workers prepared a series of chiral amino azides, employing a biphasic reaction media of H2SO4/toluene:
    • 46b Roy HH, Pitchaiah A, Kim M, Hwang IT, Lee K.-I. RSC Adv. 2013; 3: 3526
    • 46c Sadu VS, Roy HN, Arigala P, Hwang I.-T, Lee K.-I. Bull. Korean Chem. Soc. 2014; 35: 1605

    • Other groups have also evaluated (S)-2-(azidodiphenylmethyl)pyrrolidine and derivatives:
    • 46d Shi Z, Tan B, Leong WW. Y, Zeng X, Lu M, Zhong G. Org. Lett. 2010; 12: 5402
    • 46e Vinayagam P, Vishwanath M, Kesavan K. Tetrahedron: Asymmetry 2014; 25: 568 ; correction: Tetrahedron: Asymmetry 2014, 25, 1252.
    • 46f Gleeson O, Gun’ko YK, Connon SJ. Synlett 2013; 24: 1728
    • 46g Sema HA, Bez G, Karmakar S. Appl. Organomet. Chem. 2014; 28: 290
  • 47 Klumpp DA, Aguirre SL, Sanchez GV. Jr, De Leon SJ. Org. Lett. 2001; 3: 2781
  • 48 The low enantioinduction may be due to the unsuccessful formation of a diazaborolidine from the N-ethylated derivative. Unpublished observations.
  • 49 Hosoda N, Kamito H, Takano M, Takebe Y, Yamaguchi Y, Asami M. Tetrahedron 2013; 69: 1739
  • 50 Chauhan MS, Singh S. J. Mol. Catal. A: Chem. 2015; 398: 184
  • 51 Shin SH, Baek EH, Hwang G.-S, Ryu DH. Org. Lett. 2015; 17: 4746
  • 52 Lee SI, Hwang G.-S, Ryu DH. J. Am. Chem. Soc. 2013; 135: 7126
  • 53 Kang BC, Nam DG, Hwang G.-S, Ryu DH. Org. Lett. 2015; 17: 4810
  • 54 Mahender Reddy K, Bhimireddy E, Thirupathi B, Breitler S, Yu S, Corey EJ. J. Am. Chem. Soc. 2016; 138: 2443
    • 55a Fingerhut A, Serdyuk OV, Tsogoeva SB. Green Chem. 2015; 17: 2042
    • 55b Davis RL, Stiller J, Naicker T, Jiang H, Jørgensen KA. Angew. Chem. Int. Ed. 2014; 53: 7406
  • 56 Aggarwal VK, Lopin C, Sandrinelli F. J. Am. Chem. Soc. 2003; 125: 7596
    • 57a Ho C.-Y, Chen Y.-C, Wong M.-K, Yang D. J. Org. Chem. 2005; 70: 898
    • 57b An improved synthesis of (S)-2-(fluorodiphenylmethyl)pyrrolidine (S)-69 can be found in: Sparr C, Tanzer E.-M, Bachmann J, Gilmour R. Synthesis 2010; 1394
    • 58a Sparr C, Schweizer WB, Senn HM, Gilmour R. Angew. Chem. Int. Ed. 2009; 48: 3065
    • 58b Zimmer LE, Sparr C, Gilmour R. Angew. Chem. Int. Ed. 2011; 50: 11860
  • 59 Cf Juaristi E, Notario R. J. Org. Chem. 2016; 81: 1192
    • 60a Lattanzi A. Adv. Synth. Catal. 2006; 348: 339
    • 60b Lattanzi A, Russo A. Tetrahedron 2006; 62: 12264
    • 60c Russo A, Lattanzi A. Eur. J. Org. Chem. 2008; 2767
    • 60d Lattanzi A. Chem. Commun. 2009; 1452
    • 60e Russo A, Lattanzi A. Synthesis 2009; 1551
    • 60f Lattanzi A. Curr. Org. Synth. 2008; 5: 186
    • 60g Marqués-López E, Herrera RP. Curr. Org. Chem. 2011; 15: 2311
  • 61 Lu X, Liu Y, Sun B, Cindric B, Deng L. J. Am. Chem. Soc. 2008; 130: 8134
  • 62 Schmid MB, Zeitler K, Gschwind RM. J. Am. Chem. Soc. 2011; 133: 7065
  • 63 Franzén J, Marigo M, Fielenbach D, Wabnitz TC, Kjærsgaard A, Jørgensen KA. J. Am. Chem. Soc. 2005; 127: 18296
    • 64a Hayashi Y, Samanta S, Itoh T, Ishikawa H. Org. Lett. 2008; 10: 5581
    • 64b Itoh T, Ishikawa H, Hayashi Y. Org. Lett. 2009; 11: 3854
    • 64c Boeckman RK. Jr, Miller JR. Org. Lett. 2009; 11: 4544
    • 64d Urushima T, Yasui Y, Ishikawa H, Hayashi Y. Org. Lett. 2010; 12: 2966
    • 64e Hayashi Y, Shomura H, Xu Q, Lear MJ, Sato I. Eur. J. Org. Chem. 2015; 4316
    • 64f Boeckman RK. Jr, Biegasiewicz KF, Tusch DJ, Miller JR. J. Org. Chem. 2015; 80: 4030
    • 65a Zhao G.-L, Córdova A. Tetrahedron Lett. 2006; 47: 7417
    • 65b Ibrahem I, Córdova A. Chem. Commun. 2006; 1760
    • 65c Hayashi Y, Okano T, Itoh T, Urushima T, Ishikawa H, Uchimaru T. Angew. Chem. Int. Ed. 2008; 47: 9053
    • 65d Fustero S, Mojarrad F, Pérez Carrión MD, Sanz-Cervera JF, Aceña JL. Eur. J. Org. Chem. 2009; 5208
    • 65e Gómez-Bengoa E, Maestro M, Mielgo A, Otazo I, Palomo C, Velilla I. Chem. Eur. J. 2010; 16: 5333
    • 65f Galzerano P, Agostino D, Bencivenni G, Sambri L, Bartoli G, Melchiorre P. Chem. Eur. J. 2010; 16: 6069
    • 65g Kumaraswamy G, Jayaprakash N, Sridhar B. J. Org. Chem. 2010; 75: 2745
    • 65h Urushima T, Ishikawa H, Hayashi Y. Chem. Eur. J. 2011; 17: 8273
    • 65i Gómez-Bengoa E, Jiménez J, Lapuerta I, Mielgo A, Oiarbide M, Otazo I, Velilla I, Vera S, Palomo C. Chem. Sci. 2012; 3: 2949
    • 65j Hayashi Y, Sakamoto D, Shomura H, Hashizume D. Chem. Eur. J. 2013; 19: 7678
    • 65k Meyer D, Marti R, Seebach D. Eur. J. Org. Chem. 2015; 4883
    • 66a Zu L, Li H, Wang J, Yub X, Wang W. Tetrahedron Lett. 2006; 47: 5131
    • 66b García-García P, Ladépêche A, Halder R, List B. Angew. Chem. Int. Ed. 2008; 47: 4719
    • 66c Hayashi Y, Itoh T, Ohkubo M, Ishikawa H. Angew. Chem. Int. Ed. 2008; 47: 4722
    • 66d Zheng Z, Perkins BL, Ni B. J. Am. Chem. Soc. 2010; 132: 50
    • 66e Mager I, Zeitler K. Org. Lett. 2010; 12: 1480
    • 66f Wang L, Zhang X, Ma D. Tetrahedron 2012; 68: 7675
    • 66g Wang C, Yang X, Enders D. Chem. Eur. J. 2012; 18: 4832
    • 66h Chen J, Geng Z.-C, Li N, Huang X.-F, Pan F.-F, Wang X.-W. J. Org. Chem. 2013; 78: 2362
    • 66i Chen H, Zhang D, Xue F, Qin Y. Tetrahedron 2013; 69: 3141
    • 66j Feu KS, De la Torre AF, Silva S, De Moraes MA. F. Jr, Corrêa AG, Paixão MW. Green Chem. 2014; 16: 3169
    • 66k Lou Y, Xu Y, Chai Z, Shao X, Zhao G, Li Z. Tetrahedron 2015; 71: 6651
    • 67a Fan X, Sayalero S, Pericàs MA. Adv. Synth. Catal. 2012; 354: 2971
    • 67b Palomo C, Vera S, Velilla I, Mielgo A, Gómez-Bengoa E. Angew. Chem. Int. Ed. 2007; 46: 8054
    • 68a Marigo M, Wabnitz TC, Fielenbach D, Jørgensen KA. Angew. Chem. Int. Ed. 2005; 44: 794
    • 68b Marigo M, Fielenbach D, Braunton A, Kjærsgaard A, Jørgensen KA. Angew. Chem. Int. Ed. 2005; 44: 3703
    • 68c Hayashi Y, Gotoh H, Hayashi T, Shoji M. Angew. Chem. Int. Ed. 2005; 44: 4212
    • 68d Marigo M, Schulte T, Franzén J, Jørgensen KA. J. Am. Chem. Soc. 2005; 127: 15710
    • 68e Zhuang W, Marigo M, Jørgensen KA. Org. Biomol. Chem. 2005; 3: 3883

      Varied reports from diverse research groups:
    • 69a Ibrahem I, Santoro S, Himo F, Córdova A. Adv. Synth. Catal. 2011; 353: 245
    • 69b Lin S, Deiana L, Zhao G.-L, Sun J, Córdova A. Angew. Chem. Int. Ed. 2011; 50: 7624
    • 69c Riguet E. J. Org. Chem. 2011; 76: 8143
    • 69d Weng J, Li J.-M, Li F.-Q, Xie Z.-S, Lu G. Adv. Synth. Catal. 2012; 354: 1961
    • 69e Pou A, Moyano A. Eur. J. Org. Chem. 2013; 3103

      Interesting and innovative applications are compiled in the following reviews:
    • 70a ‘The Diarylprolinol Silyl Ethers: Ten Years After’: Donslund BS, Johansen TK, Poulsen PH, Haskov KS, Jørgensen KA. Angew. Chem. Int. Ed. 2015; 54: 13860
    • 70b ‘Merging Transition-Metal Activation and Aminocatalysis’: Meazza M, Ríos R. Synthesis 2016; 48: 960
    • 70c ‘Combined Asymmetric Aminocatalysis and Carbene Catalysis’: Gu J, Du W, Chen Y.-C. Synthesis 2015; 47: 3451
    • 70d ‘Enantioselective Organocatalyzed Domino Synthesis of Six-Membered Carbocycles’: Goudedranche S, Raimondi W, Bugaut X, Constantineux T, Bonne D. Synthesis 2013; 45: 1909
  • 71 Bertelsen S, Jørgensen KA. Chem. Soc. Rev. 2009; 38: 2178
    • 72a Pihko PM, Majander I, Erkkilä A. Top. Curr. Chem. 2010; 291: 29

    • Other pyrrolidine derivatives with bulky substituents in the 2-position also directs the enamine attack from the opposite face such as 2-tritylpyrrolidine described in:
    • 72b Kano T, Mii H, Maruoka K. J. Am. Chem. Soc. 2009; 131: 3450
    • 72c Kano T, Shirozu F, Maruoka K. Org. Lett. 2014; 16: 1530
    • 72d Bauer JO, Stiller J, Marqués-López E, Strohfeldt K, Christmann M, Strohmann C. Chem. Eur. J. 2010; 16: 12553
  • 73 Chi Y, Gellman SH. J. Am. Chem. Soc. 2006; 128: 6804
  • 74 Ibrahem I, Zhao G.-L, Córdova A. Chem. Eur. J. 2007; 13: 683
  • 76 Blarer SJ, Schweizer WB, Seebach D. Helv. Chim. Acta 1982; 65: 1637
  • 77 List B, Pojarliev P, Martin HJ. Org. Lett. 2001; 3: 2423
  • 78 Betancort JM, Barbas III CF. Org. Lett. 2001; 3: 3737
  • 79 Reyes-Rangel G, Vargas-Caporali J, Juaristi E. Tetrahedron 2016; 72: 379
  • 80 See: Jung ME, Piizzi G. Chem. Rev. 2005; 105: 1735
  • 81 Mečiarová M, Toma Š, Šebesta R. Tetrahedron: Asymmetry 2009; 20: 2403
  • 82 See: Hernández JG, Juaristi E. Chem. Commun. 2012; 48: 5396