ChemInform Abstract: Synthesis of β‐Silyl Ketones via Reaction of Trimethylsilyllithium with Unsaturated Hydrazones. Application to the Synthesis of Brevicomin.

Abstract

In contrast to the corresponding enolate, the metalloenamine obtained from (IV) + (II) undergoes α‐alkylation in a regio‐ and stereoselective fashion even with less reactive electrophiles such as (III) and (V), thus giving access to the desired trans‐α‐alkyl‐β‐silyl ketones (six examples given).