Novel chemoselective tosylation of the alcoholic hydroxyl group of syn-alpha,beta-disubstituted beta-hydroxy carboxylic acids.
[small beta]-Hydroxy acids were readily converted into [small beta]-tosyloxy acids (hydroxyl group activation) in moderate to excellent yields via the O,O-dianions generated by treatment with methyllithium and thus make it possible to prepare anti[small alpha],[small beta]-disubstituted [small beta]-lactones directly from the syn aldols.
Wu
Yikang
Y
State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China. yikangwu@mail.sioc.ac.cn
Sun
Ya-Ping
YP
D000438:Alcohols / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D006900:Hydroxylation; D015394:Molecular Structure
D000438:Alcohols; D002264:Carboxylic Acids