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Volumn 62, Issue 6, 2006, Pages 1043-1062

Recent advances in the Stevens rearrangement of ammonium ylides. Application to the synthesis of alkaloid natural products

Author keywords

Amines; Ammonium 1,2 Shift; Ylide

Indexed keywords

ALKALOID; ALKALOID DERIVATIVE; AMINE; AMMONIA; AMMONIUM DERIVATIVE; ANTIVIRUS AGENT; BENZAZOCINE DERIVATIVE; CARBENOID; LUPININE; NITROGEN;

EID: 29744470611     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.09.123     Document Type: Review
Times cited : (163)

References (113)
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    • For a discussion of the isolation of homodimers from oxonium ylide [1,2]-shift reactions, see: T.H. Eberlein, F.G. West, and R.W. Tester J. Org. Chem. 57 1992 3479 3482
    • (1992) J. Org. Chem. , vol.57 , pp. 3479-3482
    • Eberlein, T.H.1    West, F.G.2    Tester, R.W.3
  • 19
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    • note
    • (c) Ref. 5.
  • 45
    • 0000550687 scopus 로고    scopus 로고
    • For reviews regarding metallocarbene-mediated processes, see: (d) A. Padwa, and M.D. Weingarten Chem. Rev. 96 1996 223 269
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    • Padwa, A.1    Weingarten, M.D.2
  • 49
    • 27344444648 scopus 로고    scopus 로고
    • P.A. Evans Wiley-VCH Weinheim
    • For an overview of the use of rhodium carbenes to effect [1,2]-shift reactions of ammonium and oxonium ylides, see: F.G. West P.A. Evans Modern Rhodium Catalyzed Organic Reactions 2005 Wiley-VCH Weinheim 417 429
    • (2005) Modern Rhodium Catalyzed Organic Reactions , pp. 417-429
    • West, F.G.1
  • 51
    • 29744447765 scopus 로고    scopus 로고
    • note
    • (b) See Ref. 10b for similar difficulties with Rh(II)-catalyzed decomposition of diazo carbonyl compounds.
  • 56
    • 0031562379 scopus 로고    scopus 로고
    • For a review of carbene approaches towards α-amino acid derivatives, see: F. Zaragoza Tetrahedron 53 1997 3425 3439
    • (1997) Tetrahedron , vol.53 , pp. 3425-3439
    • Zaragoza, F.1
  • 62
    • 0030907664 scopus 로고    scopus 로고
    • (b) For a similar study on ammonium versus oxonium ylide formation see: C.O. Kappe Tetrahedron Lett. 38 1997 3323 3326
    • (1997) Tetrahedron Lett. , vol.38 , pp. 3323-3326
    • Kappe, C.O.1
  • 71
    • 0032508006 scopus 로고    scopus 로고
    • For an example of a competing [1,2]-shift observed with allyl-substituted ammonium ylides, see: (a) L.S. Beall, and A. Padwa Tetrahedron Lett. 39 1998 4159 4162
    • (1998) Tetrahedron Lett. , vol.39 , pp. 4159-4162
    • Beall, L.S.1    Padwa, A.2
  • 87
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    • note
    • For other recent examples of diastereoselective rearrangements involving the [1,2]-shift of nonstabilized ammonium ylides, see Ref. 45. For examples using stabilized ammonium ylides, see Refs. 37-39.
  • 89
    • 29744453343 scopus 로고    scopus 로고
    • note
    • This argument of possible nitrogen invertomers and metal carbenoid approach has been the rationale for explaining the stereochemical outcome of these ring-expansion reactions. This argument was discussed by West and co-workers (see Ref. 39) and has since then been discussed by Clark and co-workers (Ref. 37) and by McMills (Ref. 38).
  • 95
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    • For reports concerning preferential formation of carbonyl ylides over their amide derived ammonium counterparts see: (a) O. Peters, and W. Friedrechsen Tetrahedron Lett. 36 1995 8581 8582
    • (1995) Tetrahedron Lett. , vol.36 , pp. 8581-8582
    • Peters, O.1    Friedrechsen, W.2
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    • note
    • (e) For results where reaction conditions can provide desired products from either ylide formation see Refs. 34 and 35.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.