Stereoselectivity in the synthesis of 2-azetidinones from ketenes and imines via the staudinger reaction

Abstract

The 2-azetidinone (â-lactam) group is a crucial structural feature of one class of significant antibiotics. Its stereochemistry is very important to their biological activities. Stereoselectivity is one of the important issues in the synthesis of 2-azetidines from ketenes and imines via the Staudinger reaction. The origin of the diastereoselectivity in the reaction and influences of reaction conditions on the diastereoselectivity are reviewed. This will provide useful information for understanding and controlling the diastereoselectivity in the preparation of structurally defined 2-azetidinone derivatives.