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Volumn 36, Issue 12, 1997, Pages 1317-1319

Asymmetric Aziridination over Ylides: Highly Stereoselective Synthesis of Acetylenyl-N-sulfonylaziridines

Author keywords

Asymmetric synthesis; Aziridines; Sulfur; Ylides

Indexed keywords


EID: 0030794320     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199713171     Document Type: Article
Times cited : (102)

References (39)
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    • Asymmetric epoxidation: a) D. Yang, Y.-C. Yip, M.-W. Tang, M.-K. Wong, J.-H. Zheng, K.-K. Cheung, J. Am. Chem. Soc. 1996, 118, 491; b) V. K. Aggarwal, M. F. Wang, Chem. Commun. 1996, 191; c) Y. Tu, Z.-X. Wang, Y. Shi, J. Am. Chem. Soc. 1996, 118, 9806.
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    • Aggarwal, V.K.1    Wang, M.F.2
  • 22
    • 0029860777 scopus 로고    scopus 로고
    • Asymmetric epoxidation: a) D. Yang, Y.-C. Yip, M.-W. Tang, M.-K. Wong, J.-H. Zheng, K.-K. Cheung, J. Am. Chem. Soc. 1996, 118, 491; b) V. K. Aggarwal, M. F. Wang, Chem. Commun. 1996, 191; c) Y. Tu, Z.-X. Wang, Y. Shi, J. Am. Chem. Soc. 1996, 118, 9806.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 9806
    • Tu, Y.1    Wang, Z.-X.2    Shi, Y.3
  • 25
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    • and references therein
    • Insertion of nitrene into an allylic C-H bond was observed by the reaction with an aliphatic alkene: P. Müller, C. Baud, Y. Jacquier, Tetrahedron 1996, 52, 1543, and references therein.
    • (1996) Tetrahedron , vol.52 , pp. 1543
    • Müller, P.1    Baud, C.2    Jacquier, Y.3
  • 26
    • 0001334291 scopus 로고    scopus 로고
    • V. K. Aggarwal, A. Thompson, R. V. H. Jones, M. C. H. Standen, J. Org. Chem. 1996, 61, 8368; for a corresponding epoxidation, see V. K., Aggarwal, J. G. Ford, A. Thompson, R. V. H. Jones, M. C. H. Standen, J. Am. Chem. Soc. 1996, 118, 7004.
    • (1996) J. Org. Chem. , vol.61 , pp. 8368
    • Aggarwal, V.K.1    Thompson, A.2    Jones, R.V.H.3    Standen, M.C.H.4
  • 34
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    • note
    • We have shown that N-sulfonylimine-based aziridination is applicable to either semistable (including allylic, propargylic, and benzylic), reactive (simple alkyl ylides), and stabilized ylides (substituted with electron-withdrawing groups). Other reactive imines and activation methods of common imines also undergo this aziridination reaction.
  • 36
    • 0000641108 scopus 로고    scopus 로고
    • see also ref. [14]
    • Prepared according to literature methods: a) R. J. Goodridge, T. W. Hambley, R. K. Haynes, D. D. Ridley, J. Org. Chem. 1988, 53, 2881; b) see also ref. [14].
  • 37
    • 0001724430 scopus 로고
    • Rearrangement of an acetylenyl-substituted vinylaziridine by a multistep sequence: a) N. Manisse, J. Chuche, Tetrahedron 1977, 33, 2399; b) J. Am. Chem. Soc. 1977, 99, 1272.
    • (1977) Tetrahedron , vol.33 , pp. 2399
    • Manisse, N.1    Chuche, J.2
  • 38
    • 33847090113 scopus 로고
    • Rearrangement of an acetylenyl-substituted vinylaziridine by a multistep sequence: a) N. Manisse, J. Chuche, Tetrahedron 1977, 33, 2399; b) J. Am. Chem. Soc. 1977, 99, 1272.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 1272


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.