Synthesis 2012; 44(14): 2147-2154
DOI: 10.1055/s-0031-1290816
special topic
© Georg Thieme Verlag Stuttgart · New York

Y(OTf)3-Catalyzed Diastereoselective [3+2] Cycloaddition of N-Tosyl­aziridines and Imines; Efficient Synthesis of Multisubstituted Imidazolidines

Xingxing Wu
a  Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, P. R. of China
,
Junliang Zhang*
a  Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, P. R. of China
b  State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. of China, Fax: +86(21)62235039   Email: jlzhang@chem.ecnu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 21 February 2012

Accepted after revision: 09 March 2012

Publication Date:
27 April 2012 (eFirst)

Abstract

An efficient Y(OTf)3-catalyzed generation of azometh­ine ylides from donor–acceptor aziridines and their [3+2] cyclo­addition with imines was developed. The method provides facile access to multisubstituted imidazolidines, which have been extensively used in organic synthesis. Furthermore, a three-component reaction on a gram scale and an asymmetric variation were also developed in this work.

Supporting Information

 
  • References

    • For reviews on Lewis acid catalyzed cycloaddition of donor-acceptor cyclopropanes, see:

    • 1a Reissig H.-U, Zimmer R. Chem. Rev. 2003; 103: 1151
    • 1b Yu M, Pagenkopf BL. Tetrahedron 2005; 61: 321
    • 1c Xiao Y, Zhang J In Handbook of Cyclization Reactions . Vol. 2. Ma S. Wiley-VCH; Weinheim: 2010: 733
    • 1d Young IS, Kerr MA. Angew. Chem. Int. Ed. 2003; 42: 3023
    • 1e Sibi MP, Ma Z, Jasperse CP. J. Am. Chem. Soc. 2005; 127: 5764
    • 1f Young IS, Kerr MA. J. Am. Chem. Soc. 2007; 129: 1465
    • 1g Kang Y.-B, Sun X.-L, Tang Y. Angew. Chem. Int. Ed. 2007; 46: 3918
    • 1h Jackson SK, Karadeolian A, Driega AB, Kerr MA. J. Am. Chem. Soc. 2008; 130: 4196
    • 1i Pohlhaus PD, Sanders SD, Parsons AT, Li W, Johnson JS. J. Am. Chem. Soc. 2008; 130: 8642
    • 1j Parsons AT, Johnson JS. J. Am. Chem. Soc. 2009; 131: 3122
    • 4a Hyatt JA, Raynolds PW. Org. React. 1994; 45: 159
    • 4b Heimgartner H, Mloston G In Electronic Encyclopedia of Reagents in Organic Synthesis [Online] . Paquette L, Rigby J, Crich D, Wipf P. John Wiley & Sons; Chichester: 2004. Article RN0042
    • 4c Mloston G, Urbaniak K, Heimgartner H. Helv. Chim. Acta 2002; 85: 2056
    • 4d Vaultier M, Danion-Bougot R, Tonnard F, Carrie R. Bull. Soc. Chim. Fr. 1985; 5: 803
    • 4e Mamoun O, Benhaoua H. Bull. Soc. Chim. Fr. 1994; 103: 753
    • 4f Vebrel J, Cerutti E, Carrie R. C. R. Seances Acad. Sci., Ser. C 1979; 288: 265
    • 4g Grabowsky S, Pfeuffer T, Morgenroth W, Paulmann C, Schirmeister T, Luger P. Org. Biomol. Chem. 2008; 6: 2295
    • 4h Grabowsky S, Pfeuffer T, Checinska L, Weber M, Morgenroth W, Luger P, Schirmeister E. J. Org. Chem. 2007; 17: 2759
    • 4i Schirmeister T. Liebigs Ann. 1997; 9: 1895
    • 4j Person H, Luanglath K, Baudru M, Foucaud A. Bull. Soc. Chim. Fr. 1976; 11: 1989
    • 4k Pankova AS, Voronin VV, Kuznetsov MA. Tetrahedron Lett. 2009; 50: 5990
    • For Lewis acid promoted C–C bond cleavage of N-aryl-aziridine dicarboxylates leading to azomethine ylides, see:

    • 5a Vaultier M, Carrie R. Tetrahedron Lett. 1978; 1195
    • 5b Pohlhaus PD, Bowman RK, Johnson JS. J. Am. Chem. Soc. 2004; 126: 2294
  • 6 Paasche A, Arnone M, Fink RF, Schirmeister T, Engels B. J. Org. Chem. 2009; 74: 5244
    • 7a Li L, Wu X, Zhang J. Chem. Commun. 2011; 47: 5049
    • 7b Wu X, Li L, Zhang J. Chem. Commun. 2011; 47: 7824
    • 7c Li L, Zhang J. Org. Lett. 2011; 13: 5940
    • 7d Jiang Z, Wang J, Lu P, Wang Y. Tetrahedron 2011; 67: 9609
    • 8a Alper PB, Meyers C, Lerchner A, Siegel DR, Carreira EM. Angew. Chem. Int. Ed. 1999; 38: 3186
    • 8b Lerchner A, Carreira EM. J. Am. Chem. Soc. 2002; 124: 14826
    • 8c Meyers C, Carreira EM. Angew. Chem. Int. Ed. 2003; 42: 694
    • 8d Carson CA, Kerr MA. J. Org. Chem. 2005; 70: 8242
    • 8e Kang YB, Tang Y, Sun X.-L. Org. Biomol. Chem. 2006; 4: 299
    • 8f Parsons AT, Smith AG, Neel AJ, Johnson JS. J. Am. Chem. Soc. 2010; 132: 9688
    • For cycloaddition reactions of azomethine ylides to imines, see:

    • 9a Amornraksa K, Barr D, Donegan G, Grigg R, Ratananukul P, Sridharan V. Tetrahedron 1989; 45: 4649
    • 9b Groundwater PW, Sharif T, Arany A, Hibbs DE, Hursthouse MB, Garnett I, Nyerges M. J. Chem. Soc., Perkin Trans. 1 1998; 2837
    • 9c Erkizia E, Aldaba E, Vara Y, Arrieta A, Gornitzka H, Cossio FP. ARKIVOC 2005; (ix): 189
    • 9d Xie H, Zhu J, Chen Z, Li S, Wu Y. J. Org. Chem. 2010; 75: 7468
    • 10a Berlinck RG. S, Burtoloso AC. B, Kossuga MH. Nat. Prod. Rep. 2008; 25: 919
    • 10b Berlinck RG. S, Kossuga MH. Nat. Prod. Rep. 2005; 22: 516
    • 10c Pejchal V, Stepankova S, Padelkova Z, Imramovsky A, Jampilek J. Molecules 2011; 16: 7565
    • 10d De Luca L. Curr. Med. Chem. 2006; 13: 1
    • 10e Haneda S, Okui A, Ueba C, Hayashi M. Tetrahedron 2007; 63: 2414
    • 10f Nicolaou KC, Mathison CJ. N, Montagnon T. Angew. Chem. Int. Ed. 2003; 42: 4077
    • 10g Mohammadpoor-Baltork I, Zolfigol MA, Abdollahi-Aibeik M. Synlett 2004; 2803
    • 10h Ishihara M, Togo H. Synlett 2006; 227
    • 10i Huh DH, Ryu H, Kim YG. Tetrahedron 2004; 60: 9857
    • 10j Bellina F, Cauteruccio S, Fiore AD, Marchetti C, Rossi R. Tetrahedron 2008; 64: 6060
    • 10k Lucet D, Le Gall T, Mioskowski C. Angew. Chem. Int. Ed. 1998; 37: 2580
    • 10l Cardona F, Goti A. Nat. Chem. 2009; 1: 269
    • For synthesis of N-tosylaziridine dicarboxylates, see:

    • 11a Fan R, Ye Y. Adv. Synth. Catal. 2008; 350: 1526
    • 11b Fan RWang L, Ye Y, Zhang J. Tetrahedron Lett. 2009; 50: 3857
    • 12a Derdau V, Snieckus V. J. Org. Chem. 2011; 66: 1992
    • 12b Silva-Filho LC, Júnior VL, Constantino MG, José da Silva GV. Synthesis 2008; 2527
  • 13 CCDC 867532 (trans-3aa) contains the supplementary crystallographic data for this paper. These data can be ob-tained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif
    • For selected examples using t-Bu-Pybox as chiral ligand for enantioselective catalysis, see:

    • 14a Evans DA, Murry JA, Matt P, Norcross RD, Miller SJ. Angew. Chem. Int. Ed. 1995; 34: 798
    • 14b Schaus SE, Jacobsen EN. Org. Lett. 2000; 2: 1001
    • 14c Clark JS, Clarke M, Clough J, Blakea AJ, Wilsona C. Tetrahedron Lett. 2004; 45: 9447
    • 14d Wang J, Shao Z, Ding K, Yu WY, Chan AC. S. Adv. Synth. Catal. 2009; 351: 1250
    • 14e Kawatsura M, Kajita K, Hayase S, Itoh T. Synlett 2010; 889
    • 15a Chen Z, Wei L, Zhang J. Org. Lett. 2011; 13: 1170
    • 15b Wang T, Zhang J. Chem.–Eur. J. 2011; 17: 86
    • 15c Wang T, Zhang J. Chem. Commun. 2011; 47: 5578
    • 15d Zhang J, Chen Z, Wu H.-H, Zhang J. Chem. Commun. 2012; 48: 1817
    • 15e Wei L, Zhang J. Chem. Commun. 2012; 48: 2636