Control of the enantioselectivity of alkylation of phenylalanine derivatives by regulation of the aggregate structure of chiral enolate intermediates

Tetrahedron

Volumn 59, Issue 7, 2003, Pages 965-974

  Kawabata, Takeo ^a   Kawakami, Shin Pei ^a   Shimada, Shoko ^a   Fuji, Kaoru ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Aggregation; Asymmetric reaction; Dimers; Enolates

Indexed keywords

ALCOHOL DERIVATIVE; AMINO ACID; DIMER; PHENYLALANINE DERIVATIVE; SOLVENT;

ALKYLATION; ALLYLATION; ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; PRIORITY JOURNAL; REGULATORY MECHANISM; STEREOCHEMISTRY;

EID: 0037429110     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01626-5     Document Type: Article

References (26)

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26. The enhancement of ee in α-allylation of 20 is not due to a longer half-life of racemization of the enolate intermediate. The half-life to racemization of an enolate generated from 1 and KHMDS is 22 h at -78°C, which is long enough for the chiral enolate to undergo α-allylation without significant loss of enantiomeric purity.