Abstract
Starting from (S)-N,O-dibenzylmalimide (7), a versatile four-step approach to (4S,5R)-N-benzyl-4-benzyloxy-5-(α-hy-droxyalkyl)-2-pyrrolidinones 9 is reported. The method consists of Grignard reagent addition, p-toluenesulfonic acid monohydrate-mediated dehydration, one-pot epoxidation-methanol ring-opening reaction and reductive demethoxylation. 2-Pyrrolidinones 9 were obtained with excellent trans-diastereoselectivity in the pyrrolidinone ring and low diastereoselectivity at the carbinol center.
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