Issue 11, 2015

Stereoselective formation of chiral trans-4-hydroxy-5-substituted 2-pyrrolidinones: syntheses of streptopyrrolidine and 3-epi-epohelmin A

Abstract

A highly diastereoselective approach for the synthesis of trans-4-hydroxy-5-substituted 2-pyrrolidinones has been developed through an intramolecular cascade process of α-chiral aldimines using alkyl, aryl, alkynyl, and alkenyl Grignard reagents. The stereochemistry at the C-5 position of 2-pyrrolidinone after reaction with alkyl, aryl, and alkenyl Grignard reagents was solely controlled by α-alkoxy substitution. For alkynyl Grignard reagents, the stereochemistry was controlled by coordination of the α-alkoxy substitution and the stereochemistry of the sulfinamide. The utility of this one-pot cascade protocol is demonstrated by the asymmetric synthesis of streptopyrrolidine 5 and 3-epi-epohelmin A 3-epi-6.

Graphical abstract: Stereoselective formation of chiral trans-4-hydroxy-5-substituted 2-pyrrolidinones: syntheses of streptopyrrolidine and 3-epi-epohelmin A

Supplementary files

Article information

Article type
Research Article
Submitted
08 aug 2015
Accepted
03 sep 2015
First published
07 sep 2015

Org. Chem. Front., 2015,2, 1485-1499

Author version available

Stereoselective formation of chiral trans-4-hydroxy-5-substituted 2-pyrrolidinones: syntheses of streptopyrrolidine and 3-epi-epohelmin A

C. Si, Z. Mao, Y. Liu, Z. Du, B. Wei and G. Lin, Org. Chem. Front., 2015, 2, 1485 DOI: 10.1039/C5QO00250H

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