Article

Facile preparation and functionalization of chiral stabilized ylides from common chiral auxiliaries using triphenyl- phosphoranylideneketene (the Bestmann ylide) and their use in Wittig reactions.

Department of Chemistry, University of Rochester, Rochester, New York 14627-0216, USA.
The Journal of Organic Chemistry (impact factor: 4.45). 12/2006; 71(23):8969-72. DOI:10.1021/jo061732y pp.8969-72
Source: PubMed

ABSTRACT Camphor-derived lactams and other related chiral controllers have been found to react with the Bestmann ylide (triphenylphosphoranylideneketene) upon heating in toluene. The resulting parent ylides provide convenient access to a structurally diverse set of chiral stabilized ylides via functionalization. The utility of these chiral ylides for Wittig reactions has been briefly investigated and the effects of alpha-substitution noted.

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Keywords

alpha-substitution
 
Bestmann ylide
 
chiral ylides
 
convenient access
 
resulting parent ylides
 
structurally diverse
 
toluene
 
triphenylphosphoranylideneketene
 
Wittig reactions
 
ylides
 

Robert K Boeckman