Cis and trans selective 1,4-addition of a lithium dithioester enolate to 4-O-TBS-2-cyclohexenone

Alan C Spivey; Laetitia J Martin; Damian M Grainger; Jörg Ortner; Andrew J P White

doi:10.1021/ol0611090

Cis and trans selective 1,4-addition of a lithium dithioester enolate to 4-O-TBS-2-cyclohexenone

Org Lett. 2006 Aug 31;8(18):3891-4. doi: 10.1021/ol0611090.

Authors

Alan C Spivey¹, Laetitia J Martin, Damian M Grainger, Jörg Ortner, Andrew J P White

Affiliation

¹ Department of Chemistry, South Kensington Campus, Imperial College, London SW7 2AZ, United Kingdom. a.c.spivey@imperial.ac.uk

PMID: 16928031
DOI: 10.1021/ol0611090

Abstract

The 1,4-addition of the lithium enolate of methyldithioacetate (LMDTA) to (+/-)-4-O-TBS-2-cyclohexenone (3) can be varied from being highly 3,4-trans selective to being highly 3,4-cis selective simply by varying the reaction temperature. This stereodivergency allows expedient syntheses of the corresponding trans and cis methyl esters 6t and 6c and derived bicyclic ketolactones 7t and 7c.

Publication types

Research Support, Non-U.S. Gov't