Stereoselective synthesis of tetrasubstituted alkenes via a sequential carbocupration and a new sulfur-lithium exchange.

ABSTRACT: We have designed a new sequential carbocupration and sulfur-lithium exchange that leads stereo- and regioselectively to trisubstituted alkenyllithiums. Subsequent trapping with various electrophiles yields tetrasubstituted olefins with good control of the double-bond geometry (E/Z ratio up to 99:1). The novel sulfur-lithium exchange could be extended to the stereoselective preparation of Z-styryl lithium derivatives with almost complete retention of the double-bond geometry.

SUBMITTER: Unsinn A 

PROVIDER: S-EPMC3556915 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature