Tandem chain extension-aldol reaction: syn selectivity with a zinc enolate.
A tandem chain extension-aldol reaction was developed in which beta-keto esters are transformed to alpha-substituted-gamma-keto esters in an efficient zinc-mediated, one-pot reaction. The diastereoselectivity of the reaction ranged from good to excellent with syn stereochemistry observed for beta-keto ester and amide substrates and anti-stereochemistry observed for a beta-keto imide. [reaction: see text]
Lai
S
S
Department of Chemistry, University of New Hampshire, Durham, NH 03824, USA.
Zercher
C K
CK
Jasinski
J P
JP
Reid
S N
SN
Staples
R J
RJ
D000447:Aldehydes / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
D000447:Aldehydes; D015032:Zinc