Synthesis of Atropisomeric MeOBIPHEP Analogues and Their Application in Silver-Catalyzed Cycloisomerization of Allenols

In memory of Professor Jean Normant with deep and profound respect

Abstract

The preparation of novel MeOBIPHEP atropisomeric chiral congener ligands via an efficient palladium-catalyzed P–C coupling key step is described. We demonstrate that these palladium-catalyzed conditions are compatible with the brominated MeOBIPHEP backbone. The reaction conditions for asymmetric silver-catalyzed cycloisomerization of γ-allenols were optimized, leading to the first enantioselective catalytic system employing atropisomeric diphosphine ligands as the chiral inducer. The process follows a major 5-exo cyclization via addition of the alcohol moiety to the π-activated allenyl intermediate, leading to vinyltetrahydrofurans with enantiomeric ratios up to 91.5:8.5.

Key words

silver - cycloisomerization - allenols - asymmetric catalysis - atropisomeric ligands

• References

• 1a Trost BM, Krische MJ. Synlett 1998; 1
• 1b Lloyd-Jones GC. Org. Biomol. Chem. 2003; 1: 215
• 1c Rubin M, Sromek AW, Gevorgyan V. Synlett 2003; 2265
• 1d Marinetti A, Jullien H, Voituriez A. Chem. Soc. Rev. 2012; 41: 4884
• 1e Yamamoto Y. Chem. Rev. 2012; 112: 4736
• 1f Aubert C, Buisine O, Malacria M. Chem. Rev. 2002; 102: 813
• 1g Zhang L, Sun J, Kozmin S. Adv. Synth. Catal. 2006; 348: 2271
• 1h Michelet V, Toullec PY, Genêt J.-P. Angew. Chem. Int. Ed. 2008; 47: 4268
• 1i Jiménez-Núñez E, Echavarren AM. Chem. Rev. 2008; 108: 3326
• 1j Belmont P, Parker E. Eur. J. Org. Chem. 2009; 6075
• 1k Lee SI, Chatani N. Chem. Commun. 2009; 371
• 1l Toullec PY, Michelet V. Top. Curr. Chem. 2011; 302: 31
• 1m Zhang D.-H, Zhang Z, Shi M. Chem. Commun. 2012; 48: 10271
• 1n Obradors C, Echavarren AM. Acc. Chem. Res. 2014; 47: 902
• 2a Muratore ME, Homs A, Obradors C, Echavarren AM. Chem. Asian J. 2014; 9: 3066
• 2b Xie J, Pan C, Abdukader A, Zhu C. Chem. Soc. Rev. 2014; 43: 5245
• 2c Huang H, Zhou Y, Liu H. Beilstein J. Org. Chem. 2011; 7: 897
• 2d Lopez F, Mascarenas JL. Beilstein J. Org. Chem. 2011; 7: 1075
• 2e Hopkinson MN, Gee AD, Gouverneur V. Chem. Eur. J. 2011; 17: 8248
• 2f Hashmi AS. K, Häffner T, Rodolph M, Rominger F. Chem. Eur. J. 2011; 17: 8195
• 2g Hashmi AS. K, Blanco Jaimes MC, Schuster AM, Rominger F. J. Org. Chem. 2012; 77: 6394
• 2h Hashmi AS. K, Graf K, Ackermann M, Rominger F. ChemCatChem 2013; 5: 1200
• 2i Zhang D.-H, Tang X.-Y, Shi M. Acc. Chem. Res. 2014; 47: 913
• 2j Garayable D, Nevado C. ACS Catal. 2012; 2: 1462
• 2k Umland KD, Kirsch SF. Synlett 2013; 24: 1471
• 2l Ohno H. Isr. J. Chem. 2013; 53: 869
• 2m Qian D, Zhang J. Chem. Rec. 2014; 14: 280
• 2n Michelet V. Top. Curr. Chem. 2015; 357: 95
• 2o Dorel R, Echavarren AM. Chem. Rev. 2015; 115: 9028
• 2p Pradal A, Toullec PY, Michelet V. Synthesis 2011; 1501
• 2q Zi W, Toste FD. Chem. Soc. Rev. 2016; in press; DOI: 10.1039/C5CS00929D
• 3a Landor SR. The Chemistry of Allenes . Academic; London: 1982
• 3b Schuster HF, Coppola GM. Allenes in Organic Synthesis . Wiley; New York: 1984
• 3c Pasto DJ. Tetrahedron 1984; 40: 2805
• 3d Zimmer R, Dinesh CU, Nandanan E, Khan FA. Chem. Rev. 2000; 100: 3067
• 3e Hashmi AS. K. Angew. Chem. Int. Ed. 2000; 39: 3590
• 3f Hoffmann-Roder A, Krause N. Angew. Chem. Int. Ed. 2004; 43: 1196
• 3g Krause N, Hashmi AS. K. Modern Allene Chemistry . Wiley-VCH; Weinheim: 2004
• 3h Ma S. Chem. Rev. 2005; 105: 2829
• 3i Brummond KM, De Forrest JE. Synthesis 2007; 795
• 3j Inagaki F, Kitagaki S, Mukai C. Synlett 2011; 594
• 3k Krause N, Winter C. Chem. Rev. 2011; 111: 1994
• 3l Aubert C, Fensterbank L, Garcia P, Malacria M, Simonneau A. Chem. Rev. 2011; 111: 1954

For gold, see:
• 4a Modern Gold Catalyzed Synthesis . Hashmi AS. K, Toste FD. Wiley-VCH; Weinheim: 2012
• 4b Gold Catalysis: An Homogeneous Approach . Toste FD, Michelet V. Imperial College Press; London: 2014

For silver, see:
• 4c Lipshutz BH, Yamamoto Y. Chem. Rev. 2008; 108: 2793
• 4d Weibel J.-M, Blanc A, Pale P. Chem. Rev. 2008; 108: 3149
• 4e Alvarez-Coral M, Munoz-Dorado M, Rodriguez-Garcia I. Chem. Rev. 2008; 108: 3174
• 4f Tamamoto Y. Chem. Rev. 2008; 108: 3199
• 4g Dias HV. R, Lovely CJ. Chem. Rev. 2008; 108: 3223
• 4h Diaz-Requejo M, Perez PJ. Chem. Rev. 2008; 108: 3379
• 4i Patil NT, Yamamoto Y. Chem. Rev. 2008; 108: 3395
• 4j Silver in Organic Chemistry . Harmata M. John Wiley & Sons, Inc; New York: 2010

For gold, see:
• 5a Ilg MK, Wolf LM, Mantilli L, Farès C, Thiel W, Fürstner A. Chem. Eur. J. 2015; 21: 12279
• 5b Cox N, Uehling MR, Haeslig KT, Lalic G. Angew. Chem. Int. Ed. 2013; 52: 4878
• 5c Hamilton GL, Kang EJ, Toste FD. Science 2007; 317: 496
• 5d Zhang Z, Widenhoefer RA. Angew. Chem. Int. Ed. 2007; 46: 283
• 5e Aikawa K, Kojima M, Mikami K. Adv. Synth. Catal. 2010; 352: 3131

For silver, see:
• 5f Wang Y, Zheng K, Hong R. J. Am. Chem. Soc. 2012; 134: 4096
• 5g Arbour JL, Rzepa HS, Contreras-García J, Adrio LA, Barreiro EM, Hii KK. Chem. Eur. J. 2012; 18: 11317
• 6 Naodovic M, Yamamoto H. Chem. Rev. 2008; 108: 3132
• 7a Chao C.-M, Beltrami D, Toullec PY, Michelet V. Chem. Commun. 2009; 6988
• 7b Pradal A, Chao C.-M, Beltrami D, Toullec PY, Michelet V. Beilstein J. Org. Chem. 2011; 7: 1021
• 7c Pradal A, Chen Q, Faudot dit Bel P, Toullec PY, Michelet V. Synlett 2012; 23: 74
• 7d Chao C.-M, Toullec PY, Michelet V. Tetrahedron Lett. 2009; 50: 3719
• 7e Toullec PY, Blarre T, Michelet V. Org. Lett. 2009; 11: 2888
• 7f Chao C.-M, Vitale MR, Toullec PY, Genêt J.-P, Michelet V. Chem. Eur. J. 2009; 15: 1319
• 7g Leseurre L, Toullec PY, Genêt J.-P, Michelet V. Org. Lett. 2007; 9: 4049
• 7h Antoniotti S, Genin E, Michelet V, Genêt J.-P. J. Am. Chem. Soc. 2005; 127: 9976
• 7i Neatu F, Li Z, Richards R, Toullec PY, Genêt J.-P, Dumbuya K, Gottfried JM, Steinrück H.-P, Pârvulescu VI, Michelet V. Chem. Eur. J. 2008; 14: 9412
• 7j Tomas-Mendivil E, Toullec PY, Borge J, Conejero S, Michelet V, Cadierno V. ACS Catal. 2013; 3: 3086
• 7k Arcadi A, Pietropaolo E, Alvino A, Michelet V. Org. Lett. 2013; 15: 2766
• 7l Tomas-Mendivil E, Starck J, Ortuno J.-C, Michelet V. Org. Lett. 2015; 17: 6126
• 7m Carrër A, Péan C, Perron-Sierra F, Mirguet O, Michelet V. Adv. Synth. Catal. 2016; 358: 1540
• 8a Mariaule G, Newsome G, Toullec PY, Belmont P, Michelet V. Org. Lett. 2014; 16: 4570
• 8b Arcadi A, Chiarini M, Del Vecchio L, Marinelli F, Michelet V. Chem. Commun. 2016; 52: 1458
• 8c Bontemps A, Mariaule G, Desbène-Finck S, Helissey P, Giorgi-Renault S, Michelet V, Belmont P. Synthesis 2016; 48: 2178
• 9a Schmidt R, Scalone M, Michelet V, Scalone M. (R)- and (S)-2,2′-Bis(diphenylphosphino)-6,6′-dimethoxy-1,1′-biphenyl . In e-EROS Encyclopedia of Reagents for Organic Synthesis . Paquette L, Fuchs P, Crich D, Wipf P. John Wiley & Sons; New York: 2015. DOI: 10.1002/047084289X.rn00832.pub2
• 9b Leseurre L, Le Boucher d’Herouville F, Püntener K, Scalone M, Genêt J.-P, Michelet V. Org. Lett. 2011; 13: 3250
• 9c Leseurre L, Le Boucher d’Herouville F, Millet A, Genêt J.-P, Scalone M, Michelet V. Catal. Commun. 2015; 69: 129
• 9d Leseurre L, Püntener K, Genêt J.-P, Scalone M, Michelet V. Adv. Synth. Catal. 2011; 353: 3269
• 9e Le Boucher d’Herouville F, Millet A, Scalone M, Michelet V. J. Org. Chem. 2011; 76: 6925
• 10 Wadamoto M, Yamamoto H. J. Am. Chem. Soc. 2005; 127: 14556
• 11a Laue C, Schröder G, Arlt D (Bayer AG) EP 749973 A1, 1996
• 11b Drießen-Holscher B, Kralik J, Agel F, Steffens C, Hu C. Adv. Synth. Catal. 2004; 346: 979
• 11c Malcolmson SJ, Meek SJ, Sattely ES, Schrock RR, Hoveyda AH. Nature 2008; 456: 933
• 11d Meek SJ, O’Brien RV, Llaveria J, Schrock RR, Hoveyda AH. Nature 2011; 471: 461
• 11e Sattley ES, Meek SJ, Malcolmson SJ, Schrock RR, Hoveyda AH. J. Am. Chem. Soc. 2009; 131: 943
• 12 For the bromination of 3-aminoethylphosphonate, see: Beugelmans R, Chbani M. Bull. Soc. Chim. Fr. 1995; 132: 290
• 13 Uson R, Laguna A, Laguna M. Inorg. Synth. 1989; 26: 85
• 14 Arbour JL, Rzepa HS, White AJ. P, Hii KK. Chem. Commun. 2009; 7125
• 15a Godet T, Vaxelaire C, Michel C, Milet A, Belmont P. Chem. Eur. J. 2007; 13: 5632
• 15b Michel C, Godet T, Dheu-Andries M.-L, Belmont P, Milet A. J. Mol. Struct. (Theochem) 2007; 811: 175
• 15c Parker E, Leconte N, Godet T, Belmont P. Chem. Commun. 2011; 47: 343
• 16a Nagendrappa G, Joshi GC, Devaprabhakara D. J. Organomet. Chem. 1971; 27: 421
• 16b Chenier JH. B, Howard JA, Mile B. J. Am. Chem. Soc. 1985; 107: 4190
• 17a Gandon V, Lemière G, Hours A, Fensterbank L, Malacria M. Angew. Chem. Int. Ed. 2008; 47: 7534
• 17b Malacria M, Fensterbank L, Gandon V. Top. Curr. Chem. 2011; 302: 157
• 18a Brown TJ, Sugie A, Dickens MG, Widenhoefer RA. Organometallics 2010; 29: 4207
• 18b Brown TJ, Sugie A, Leed MD, Widenhoefer RA. Chem. Eur. J. 2012; 18: 6959
• 19 Zhang Z, Liu C, Kinder RE, Han X, Gian H, Widenhoefer RA. J. Am. Chem. Soc. 2006; 128: 9066