Asymmetric Nitroallylation of Arylboronic Acids with Nitroallyl Acetates Catalyzed by Chiral Rhodium Complexes and Its Application in a Concise Total Synthesis of Optically Pure (+)--Lycorane

Org. Lett., 7 (19), 4285 -4288, 2005. 10.1021/ol051795n S1523-7060(05)01795-5
Web Release Date: August 23, 2005

Asymmetric Nitroallylation of Arylboronic Acids with Nitroallyl Acetates Catalyzed by Chiral Rhodium Complexes and Its Application in a Concise Total Synthesis of Optically Pure (+)--Lycorane

Lin Dong, Yan-Jun Xu, Lin-Feng Cun, Xin Cui, Ai-Qiao Mi, Yao-Zhong Jiang, and Liu-Zhu Gong*

Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province and Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041, China, and Graduate School of Chinese, Academy of Sciences, Beijing, China

gonglz@cioc.ac.cn

Received July 28, 2005

Abstract:

A new rhodium-catalyzed highly enantioselective nitroallylation of 2-nitrocyclohex-2-enol esters with arylboronic acids is described. A rhodium complex of [RhOH(COD)]₂ and optically pure BINAP is the optimal catalyst that provides good yields and high enantioselectivities ranging from 90 to 99% ee for various arylboronic acids at 50

C. A concise total synthesis of optically pure (+)-

-lycorane in overall 38% yield was achieved on the basis of this new method.

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