The stereocontrolled construction of the adjacent tertiary carbons is important in the synthesis of various natural products. By conducting the Michael addition of ester and amide enolates to a, β-unsaturated esters under appropriate reaction conditions, glutaric acid derivatives with definite relative and absolute configuration are prepared. In combination with intramolecular carbon-carbon bond formation, the process is extended to the stereoselective formation of extracyclic chiral centers, and successfully applied to the synthesis of (+)-dehydroiridodiol. Several other approaches to the stereoselective synthesis of adjacent tertiary carbons are also included.
|Number of pages||16|
|Journal||Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry|
|Publication status||Published - 1986|
ASJC Scopus subject areas
- Organic Chemistry