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■ A Selective Synthesis of Both Enantiomers of a 1-Allyl-β-carboline Using the Same Chiral Auxiliary Derived from L-Proline

Yûji Matsuya, Takashi Itoh, Yasuko Enomoto, and Akio Ohsawa*

*School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan

Abstract

In the study of asymmetric allylation of β-carbolines, reversed stereoselectivity toward a same substrate was observed depending on allylating agents. Based on this finding, the synthesis of both enantiomers of 1-allyl-β-carbolines was accomplished on a practical level of yields and selectivities.