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Volumn 46, Issue 4, 2007, Pages 565-568

Stereoselective intermolecular formal [3+3] cycloaddition reaction of cyclic enamines and enones

Author keywords

Conjugate addition; Diastereoselectivity; Enamines; Enones; Imines

Indexed keywords

ADDITION REACTIONS; ALKYLATION; AROMATIZATION; BIOSYNTHESIS; KETONES; STEREOCHEMISTRY; UNSATURATED COMPOUNDS;

EID: 33846500851     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200603302     Document Type: Article
Times cited : (38)

References (56)
  • 9
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    • Eds, E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Berlin
    • f) Comprehensive Asymmetric Catalysis I-III (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999.
    • (1999) Comprehensive Asymmetric Catalysis I-III
  • 16
    • 0004087670 scopus 로고
    • see also:, Ed, Z. Rappoport, Wiley, Chichester
    • f) see also: P. W. Hickmott in The Chemistry of Enamines (Ed.: Z. Rappoport), Wiley, Chichester, 1994;
    • (1994) The Chemistry of Enamines
    • Hickmott, P.W.1
  • 34
    • 33846528674 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.
  • 35
    • 0034730770 scopus 로고    scopus 로고
    • Imine 13a was readily prepared by a procedure based on those described by: T. N. Van, N. De Kimpe, Tetrahedron 2000, 56, 7969;
    • Imine 13a was readily prepared by a procedure based on those described by: T. N. Van, N. De Kimpe, Tetrahedron 2000, 56, 7969;
  • 36
    • 0037050415 scopus 로고    scopus 로고
    • 103; for optimum results, 13a is stored as the corresponding HCl salt 5a to minimize oxidation by air
    • B. G. Davis, M. A. T. Maughan, T. M. Chapman, R. Villard, S. Courtney, Org. Lett. 2002, 4, 103; for optimum results, 13a is stored as the corresponding HCl salt 5a to minimize oxidation by air.
    • (2002) Org. Lett , vol.4
    • Davis, B.G.1    Maughan, M.A.T.2    Chapman, T.M.3    Villard, R.4    Courtney, S.5
  • 37
    • 33846524426 scopus 로고    scopus 로고
    • The use of heterocuprates or fewer than 1.5 equivalents of the homocuprate gave inferior results
    • The use of heterocuprates or fewer than 1.5 equivalents of the homocuprate gave inferior results.
  • 38
    • 33846558096 scopus 로고    scopus 로고
    • The isolation and purification of 10a prior to its reduction is not required, but is recommended for optimum results.
    • The isolation and purification of 10a prior to its reduction is not required, but is recommended for optimum results.
  • 39
    • 33846556313 scopus 로고    scopus 로고
    • The product of a boatlike transition state has not been observed
    • The product of a boatlike transition state has not been observed.
  • 40
    • 0030924784 scopus 로고    scopus 로고
    • The use of the corresponding O-TMS derivative of 10e was found to be optimal; for a review, see: D. Enders, U. Reinhold, Tetrahedron: Asymmetry 1997, 8, 1895.
    • The use of the corresponding O-TMS derivative of 10e was found to be optimal; for a review, see: D. Enders, U. Reinhold, Tetrahedron: Asymmetry 1997, 8, 1895.
  • 41
    • 33846482680 scopus 로고    scopus 로고
    • Competitive hydrolysis of the initial 1,4-addition product occurs during workup
    • Competitive hydrolysis of the initial 1,4-addition product occurs during workup.
  • 42
  • 44
  • 48
    • 33646468489 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 1520;
    • (2006) Chem. Int. Ed , vol.45 , pp. 1520
    • Angew1
  • 50
    • 33846484416 scopus 로고    scopus 로고
    • The suggested mode of catalysis is based on prior reports on related transformations see reference [16
    • The suggested mode of catalysis is based on prior reports on related transformations (see reference [16]).
  • 51
    • 33846500300 scopus 로고    scopus 로고
    • The use of TFE-water as the solvent mixture led to products (Table 2) with 5-10% ee.
    • The use of TFE-water as the solvent mixture led to products (Table 2) with 5-10% ee.
  • 52
    • 24944467463 scopus 로고    scopus 로고
    • A variety of modulators of cholinergic activity contain cyclic amines or amino alcohols as rigid acetylcholine analogues; see: a J. W. Clader, Y. Wang, Curr. Pharm. Design 2005, 11, 3353;
    • A variety of modulators of cholinergic activity contain cyclic amines or amino alcohols as rigid acetylcholine analogues; see: a) J. W. Clader, Y. Wang, Curr. Pharm. Design 2005, 11, 3353;
  • 55
    • 0004246896 scopus 로고    scopus 로고
    • For substrate-controlled diastereoselective conjugate addition, see: a, Ed, N. Krause, Wiley-VCH, Weinheim
    • For substrate-controlled diastereoselective conjugate addition, see: a) B. Breit, P. Demel in Modern Organocopper Chemistry (Ed.: N. Krause), Wiley-VCH, Weinheim, 2002, pp. 188-223;
    • (2002) Modern Organocopper Chemistry , pp. 188-223
    • Breit, B.1    Demel, P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.