4-(Dimethylaminomethyl)phenylacetic acid hydrochloride
CAS Number:
99985-52-1
Molecular Formula:
C11H16ClNO2
Stereoselective formation of chiral trans-4-hydroxy-5-substituted 2-pyrrolidinones: syntheses of streptopyrrolidine and 3-epi-epohelmin A
Literature Information
Publication Date
2015-09-07
DOI
10.1039/C5QO00250H
Impact Factor
5.281
Authors
Chang-Mei Si, Zhuo-Ya Mao, Yi-Wen Liu, Zhen-Ting Du, Bang-Guo Wei, Guo-Qiang Lin
View Original
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.
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Source Journal
Organic Chemistry Frontiers
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