First diastereoselective intramolecular Baylis-Hillman reaction: an easy access to chiral alpha-methylene-beta-hydroxylactones.

作者信息

Krishna Palakodety Radha, Kannan V, Sharma G V M

机构信息

D-206/B, Discovery Laboratory, Organic Chemistry Division-III, Indian Institute of Chemical Technology, Hyderabad-500 007, India.

出版信息

J Org Chem. 2004 Sep 17;69(19):6467-9. doi: 10.1021/jo049511k.

DOI:10.1021/jo049511k

PMID:15357610

Abstract

The first diastereoselective intramolecular Baylis-Hillman reaction of chiral substrates is reported wherein both aldehyde and activated olefin coexist as substituents to afford alpha-methylene-beta-hydroxylactones in good yields exclusively as single isomers under the standard base-catalyzed reaction conditions in CH(2)Cl(2). Formation of alkoxylactones by an in situ derivatization of adducts was also observed.

摘要