Stereoselective chloroacetate aldol reactions: syntheses of acetate aldol equivalents and darzens glycidic esters.
Aldol reaction of the Ti-enolate derived from cis-1-tosylamido-2-indanyl chloroacetate with representative aldehydes proceeded in excellent yield and high diastereoselectivities. Removal of chlorine provided alternative access to highly diastereoselective acetate aldol equivalents or the corresponding glycidic ester condensation products. [reaction: see text]
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607, USA. arunghos@uic.edu
Arun K
AK
Ghosh
Jae-Hun
JH
Kim
D000085:Acetates / Q000737:chemistry*; D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D004952:Esters / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry*
D000085:Acetates; D000447:Aldehydes; D004952:Esters; C006972:chloroacetic acid; C116609:3-hydroxybutanal; D014025:Titanium