Mondal, M;Ho, HJ;Peraino, NJ;Gary, MA;Wheeler, KA;Kerrigan, NJ

2013

May

Journal of Organic Chemistry

Diastereoselective Reaction of Sulfoxonium Ylides, Aldehydes and Ketenes: An Approach to trans-gamma-Lactones

Published

9 ()

ENANTIOSELECTIVE SYNTHESIS DISUBSTITUTED KETENES ASYMMETRIC-SYNTHESIS OXOSULFONIUM YLIDES ORGANIC SYNTHESIS SULFURANE OXIDES BETA-LACTAMS BUTYROLACTONES CYCLOADDITION SULFOXIMINES

78

4587

4593

In this paper, a novel approach to gamma-lactones from the reaction of sulfoxonium ylides, aldehydes, and ketenes is described. The new ylide-based method provides access to gamma-lactones from disubstituted ketenes, in good yields, and with good diastereoselectivity favoring the trans-diastereomer (11 examples with dr >= 82:18, dr up to 92:8).

WASHINGTON

0022-3263

10.1021/jo4003213