Asymmetric Friedel-Crafts Alkylation of α-Substituted β-Nitroacrylates: Access to β2,2-Amino Acids Bearing Indolic All-Carbon Quaternary Stereocenters

作者：Weng, Jian-Quan; Deng, Qao-Man; Wu, Liang; Xu, Kai; Wu, Hao; Liu, Ren-Rong; Gao, Jian-Rong; Jia, Yi-Xia^*

来源：Organic Letters, 2014, 16(3): 776-779.

DOI：10.1021/ol403480v

• MICHAEL ADDITION
• CONJUGATE ADDITION
• ENANTIOSELECTIVE SYNTHESIS
• STEREOSELECTIVE-SYNTHESIS
• BETA(2)-AMINO ACIDS
• AMINO
• NITROALKENES
• CATALYST
• CONSTRUCTION
• ENONES

A highly enantioselective Friedel-Crafts alkylation reaction of indoles with acyclic alpha-substituted beta-nitroacrylates is developed under the catalysis of Ni(ClO4)(2)-bisoxazoline complex at 1 mol % catalyst loading, affording chiral indolic beta-nitroesters bearing all-carbon quaternary stereocenters in excellent yields and ees of up to 97%. Transformation of one of the products to beta(2,2)-amino ester and tetrahydro-beta-carboline through nitro reduction and sequential Pictet-Spengler cyclization was exemplified.

• 出版日期2014-2-7
• 单位浙江工业大学