1,5-Induction in reactions between 2-alkoxy-(2-tributylstannylethylidene)cyclohexanes and aldehydes

Abstract

2-Methoxy(2-tributylstannylethylidene)cyclohexane 16 undergoes stereoselective transmetalation on treatment with tin(IV) chloride to generate the allyltin trichloride 19 which reacts with aldehydes to give the (Z)-(3-hydroxyalkylidene)-2-methoxycyclohexanes 17a-g with excellent 1,5-stereocontrol.

Keywords

• allylstannane
• stereocontrol