Highly stereoselective oxy-michael additions to beta,gamma-unsaturated alpha-keto esters: rapid enantioselective synthesis of 3-hydroxybutenolides.
The highly diastereoselective oxy-Michael addition of the "naked" anion of (6S)-methyl delta-lactol to gamma-substituted beta,gamma-unsaturated alpha-keto esters leading to the direct formation of THP*-protected gamma-hydroxy alpha-keto ester derivatives is described. Subsequent acid-mediated deprotection affords the 3-hydroxybutenolides in high yields.
Xiong
Xin
X
School of Chemistry, The University of Manchester, Oxford Road, Manchester M13 9PL, UK.
Ovens
Caroline
C
Pilling
Adam W
AW
Ward
John W
JW
Dixon
Darren J
DJ