Asymmetric nitroallylation of arylboronic acids with nitroallyl acetates catalyzed by chiral rhodium complexes and its application in a concise total synthesis of optically pure (+)-gamma-lycorane.
[reaction: see text]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 degrees C. A concise total synthesis of optically pure (+)-gamma-lycorane in overall 38% yield was achieved on the basis of this new method.
Dong
Lin
L
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041, China.
Xu
Yan-Jun
YJ
Cun
Lin-Feng
LF
Cui
Xin
X
Mi
Ai-Qiao
AQ
Jiang
Yao-Zhong
YZ
Gong
Liu-Zhu
LZ