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Volumn 43, Issue 8, 2004, Pages 1011-1014

Enantiodivergence in the reactions of a highly enantiomerically enriched silyllithium compound with benzyl halides: Control of inversion and retention by selection of halide

Author keywords

Benzyl halides; Density functional calculations; Organosilanes; Silyllithium compounds; Stereochemistry

Indexed keywords

CHEMICAL REACTIONS; SILICON COMPOUNDS;

EID: 4544233508     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352700     Document Type: Article
Times cited : (35)

References (33)
  • 13
    • 0004228992 scopus 로고
    • (Ed.: R. J. K. Taylor), Oxford University Press, Oxford (England)
    • I. Fleming in Organocopper Reagents (Ed.: R. J. K. Taylor), Oxford University Press, Oxford (England), 1994, p. 257-292.
    • (1994) Organocopper Reagents , pp. 257-292
    • Fleming, I.1
  • 14
    • 4544242658 scopus 로고    scopus 로고
    • 2 = 0.1231 (all data). The absolute configuration was determined by refinement of the Flack parameter to -0.03(3). CCDC-217658 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.can.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Centre, 12 Union Road, Cambridge CB21EZ, UK; Fax: (+44) 1223-336033; or deposit@ccdc. cam.ac.uk).
  • 15
    • 4544262189 scopus 로고    scopus 로고
    • note
    • The previously investigated optically active halosilanes reacted with organolithium compounds with inversion; especially for the benzyl anion as nucleophile inversion at the silicon center was always observed independent of the leaving group (see ref [4b] und [4c]).
  • 16
    • 4544237379 scopus 로고    scopus 로고
    • note
    • 10)X with X = Li, Cl, Br present in the reaction solutions were observed in only small amounts (< 1%) at reaction temperatures between -78 and 0°C. The fraction of these coupling products rises significantly, however, if care is not taken during the reaction procedure to ensure that the reaction solution is immediately and thoroughly mixed (particularly pronounced in the reaction with benzyl chloride at 0°C).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.