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Volumn 125, Issue 41, 2003, Pages 12412-12413

Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; ALLYL COMPOUND; AMINE; COORDINATION COMPOUND; TRICHLOROACETIMIDIC ACID;

EID: 0141885409     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja037086r     Document Type: Article
Times cited : (249)

References (32)
  • 3
    • 0141997633 scopus 로고    scopus 로고
    • comprehensive review in preparation
    • More than 170 publications report, use of this rearrangement to prepare allylic amines and analogues: Carpenter, N. E.; Overman, L. E., comprehensive review in preparation.
    • Carpenter, N.E.1    Overman, L.E.2
  • 13
    • 0141997631 scopus 로고    scopus 로고
    • note
    • Coordination of the palladium center to the π bond, not nitrogen, is required in a cyclization-induced rearrangement.
  • 22
    • 0141997630 scopus 로고    scopus 로고
    • note
    • Formation of cinnamyl trichloroacetamide presumably occurs by a competing ionization-recombination pathway.
  • 23
    • 0141962993 scopus 로고    scopus 로고
    • note
    • Using (R)-valinol, ent-5 was prepared in a manner analogous to that of 5.
  • 24
    • 0037045233 scopus 로고    scopus 로고
    • 3) is reported for a 90% ee sample of the S enantiomer of established absolute configuration, see: Overman, L. E.; Remarchuk, T. J. Am. Chem. Soc. 2002, 124, 12-13.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 12-13
    • Overman, L.E.1    Remarchuk, T.2
  • 25
    • 0026620389 scopus 로고
    • and ref 20 therein
    • 2O, pH 6.6) is reported for enantiopure 7, see: Kwon, T. W.; Keusenkothen, P. F.; Smith, M. B. J Org. Chem. 1992, 57, 6169-6173 and ref 20 therein.
    • (1992) J Org. Chem. , vol.57 , pp. 6169-6173
    • Kwon, T.W.1    Keusenkothen, P.F.2    Smith, M.B.3
  • 28
    • 0141928478 scopus 로고    scopus 로고
    • note
    • The absolute configuration of 2e was determined by X-ray analysis. Removal of the TBDMS group from (S)-2n provided (S)-2o in high yield. Absolute configurations of other allylic trichloroacetamides prepared during this investigation were assigned by analogy to 2e, 2o, 2k, and 2n.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.