title: 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.
abstract: [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.
authors.affiliation: Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041, China.
authors.forename: Lin
authors.initials: L
authors.lastname: Dong
authors.forename: Yan-Jun
authors.initials: YJ
authors.lastname: Xu
authors.forename: Lin-Feng
authors.initials: LF
authors.lastname: Cun
authors.forename: Xin
authors.initials: X
authors.lastname: Cui
authors.forename: Ai-Qiao
authors.initials: AQ
authors.lastname: Mi
authors.forename: Yao-Zhong
authors.initials: YZ
authors.lastname: Jiang
authors.forename: Liu-Zhu
authors.initials: LZ
authors.lastname: Gong