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Volumn 72, Issue 4, 2007, Pages 1294-1300

Lewis acid mediated asymmetric [2,3]-sigmatropic rearrangement of allylic amines. Scope and mechanistic investigation

Author keywords

[No Author keywords available]

Indexed keywords

IODINE COMPOUNDS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 33847000590     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062178v     Document Type: Article
Times cited : (30)

References (50)
  • 1
    • 0000033512 scopus 로고
    • Trost, B. M, Fleming, I, Eds, Pergamon: Oxford
    • Markó, I. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3. pp 913-974.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 913-974
    • Markó, I.E.1
  • 26
    • 0028911643 scopus 로고
    • For recent publications, see: a
    • For recent publications, see: (a) Clark, J. S.; Hodgson, P. B. Tetrahedron Lett. 1995, 36, 2519-2522.
    • (1995) Tetrahedron Lett , vol.36 , pp. 2519-2522
    • Clark, J.S.1    Hodgson, P.B.2
  • 34
    • 33846968013 scopus 로고    scopus 로고
    • For prior Lewis acid mediated [2,3]-sigmatropic rearrangements of allylic amines, see: (a) Murata, Y.; Nakai, K. Chem. Lett. 1990, 2069-2072.
    • For prior Lewis acid mediated [2,3]-sigmatropic rearrangements of allylic amines, see: (a) Murata, Y.; Nakai, K. Chem. Lett. 1990, 2069-2072.
  • 38
    • 33846960023 scopus 로고    scopus 로고
    • The rearrangements were repeated but gave differing ee's
    • The rearrangements were repeated but gave differing ee's.
  • 39
    • 33846998860 scopus 로고    scopus 로고
    • 4 anions during preparation of the chiral Lewis acid.
    • 4 anions during preparation of the chiral Lewis acid.
  • 42
    • 33846983780 scopus 로고    scopus 로고
    • The structures of [1,2]-rearranged 1c,e,g were confirmed by H,H-COSY.
    • The structures of [1,2]-rearranged 1c,e,g were confirmed by H,H-COSY.
  • 47
    • 33751155334 scopus 로고
    • Equilibration before deprotonation and rearrangement can also be envisioned
    • Vedejs, E.; Fields, S. C.; Lin, S.; Schrimpf, M. R. J. Org. Chem. 1995, 60, 3028-3034. Equilibration before deprotonation and rearrangement can also be envisioned.
    • (1995) J. Org. Chem , vol.60 , pp. 3028-3034
    • Vedejs, E.1    Fields, S.C.2    Lin, S.3    Schrimpf, M.R.4
  • 48
    • 33846953409 scopus 로고    scopus 로고
    • For computational details, see ref 14
    • For computational details, see ref 14.
  • 49
    • 33846991474 scopus 로고    scopus 로고
    • This procedure was necessary to remove all HBr from the reaction vessel
    • This procedure was necessary to remove all HBr from the reaction vessel.
  • 50
    • 33846946704 scopus 로고    scopus 로고
    • The reaction time could be shortened to 1-2 h by heating at 60°C.
    • The reaction time could be shortened to 1-2 h by heating at 60°C.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.