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Iridium Complex-Catalyzed Allylic Amination of Allylic Esters

Ryo Takeuchi*, Naoki Ue, Keisuke Tanabe, Kengo Yamashita and Norihito Shiga

*Department of Chemistry, Graduate School of Integrated Science, Yokohama City University, 22-2 Seto, Kanazawa-ku, Yokohama 236-0027, Japan

R. Takeuchi, N. Ue, K. Tanabe, K. Yamashita, N. Shiga, J. Am. Chem. Soc., 2001, 123, 9525-9534.

DOI: 10.1021/ja0112036


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Abstract

An iridium-catalyzed allylic amination of branched and linear allylic carbonates provides branched amines in high selectivity. The use of a polar solvent such as EtOH is essential for obtaining products in high yield. Both secondary and primary amines could be used for this reaction. When a primary amine was used, selective monoallylation occurred.


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proposed mechanism



Key Words

allylic amines


ID: J48-Y2001