Lewis acid promoted aziridination of imines with semistabilized sulfonium ylides: Highly stereoselective synthesis of vinyl- and ethynyl-aziridines

Chemical Communications

Volumn , Issue 13, 1997, Pages 1231-1232

  Wang, De Kun ^a   Dai, Li Xin ^a   Hou, Xue Long ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001465467     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a702955a     Document Type: Article

References (28)

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8. For leading references see (a) V. K. Aggarwal, A. Thompson, R. V. H. Jones and M. C. H. Standen, J. Org. Chem., 1996, 61, 8368; (b) A.-H. Li, L.-X. Dai and X.-L. Hou, Chem. Commun., 1996, 491; (c) A.-H. Li, L.-X. Dai and X.-L. Hou, J. Chem. Soc., Perkin Trans. I, 1996, 867; (d) A.-H. Li, L.-X. Dai, X.-L. Hou and M.-B. Chen, J. Org. Chem., 1996, 61, 4641; (e) A.-H. Li, L.-X. Dai and X.-L. Hou, J. Chem. Soc., Perkin Trans. I, 1996, 2725.
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23. For example, the Lewis acid is necessary in the synthesis of aziridines from imines and ethyl diazoacetate, see L. Casarrubios, J. A. Pérez, M. Brookhart and J. L. Templeton, J. Org. Chem., 1996, 61, 8358.
24. For the preparation of 3-trimethylsilylallyldiphenylsulfonium perchlorate 2m and 3-trimethylsilylprop-2-ynyldiphenylsulfonium perchlorate 2n, see T. K. Jones and S. E. Denmark, Org. Synth., 1990, Coll. Vol. 7, 524; R. W. LaRochelle, B. M. Trost and L. Krepski, J. Org. Chem., 1971, 36, 1126.
25. For the preparation of 3-trimethylsilylallyldiphenylsulfonium perchlorate 2m and 3-trimethylsilylprop-2-ynyldiphenylsulfonium perchlorate 2n, see T. K. Jones and S. E. Denmark, Org. Synth., 1990, Coll. Vol. 7, 524; R. W. LaRochelle, B. M. Trost and L. Krepski, J. Org. Chem., 1971, 36, 1126.
26. N. Mimura, T. Ibuka, M. Akaji, Y. Miwa, T. Taga, K. Nakai, H. Tamamura, N. Fujii and Y. Yamamoto, Chem. Commun., 1996, 351. The cis-selectivity phenomenon were also found; M. Komatsu, M. Ohno, S. Tsuno and Y. Ohshiro, Chem. Lett., 1990, 575. The Darzens fashion; G. Cainelli, M. Panurizio and D. Giacomini, Tetrahedron Lett., 1991, 121.
27. N. Mimura, T. Ibuka, M. Akaji, Y. Miwa, T. Taga, K. Nakai, H. Tamamura, N. Fujii and Y. Yamamoto, Chem. Commun., 1996, 351. The cis-selectivity phenomenon were also found; M. Komatsu, M. Ohno, S. Tsuno and Y. Ohshiro, Chem. Lett., 1990, 575. The Darzens fashion; G. Cainelli, M. Panurizio and D. Giacomini, Tetrahedron Lett., 1991, 121.
28. N. Mimura, T. Ibuka, M. Akaji, Y. Miwa, T. Taga, K. Nakai, H. Tamamura, N. Fujii and Y. Yamamoto, Chem. Commun., 1996, 351. The cis-selectivity phenomenon were also found; M. Komatsu, M. Ohno, S. Tsuno and Y. Ohshiro, Chem. Lett., 1990, 575. The Darzens fashion; G. Cainelli, M. Panurizio and D. Giacomini, Tetrahedron Lett., 1991, 121.