文献类型：期刊文献

英文题名：Direct Asymmetric Synthesis of β-Bis-Aryl-α-Amino Acid Esters via Enantioselective Copper-Catalyzed Addition of p-Quinone Methides

作者：He, Fu-Sheng[1,2];Jin, Jing-Hai[1,2];Yang, Zhong-Tao[1,2];Yu, Xingxin[1,2];Fossey, John S.[3];Deng, Wei-Ping[1,2]

机构：[1]E China Univ Sci & Technol, Sch Pharm, 130 Meilong Rd, Shanghai 200237, Peoples R China;[2]E China Univ Sci & Technol, Shanghai Key Lab New Drug Design, 130 Meilong Rd, Shanghai 200237, Peoples R China;[3]Univ Birmingham, Sch Chem, Birmingham B15 2TT, W Midlands, England

年份：2016

卷号：6

期号：2

起止页码：652

外文期刊名：ACS CATALYSIS

收录：;EI(收录号：20160701917415);WOS:【SCI-EXPANDED(收录号:WOS:000369774900018)】；

基金：This work is supported by The Fundamental Research Funds for the Central Universities, the National Natural Science Foundation of China (Nos. 21172068, 21572053), Shanghai Pujiang Program (No. 14PJD013), and Shanghai Yangfan Program (No. 14YF1404600). J.S.F. thanks ECUST for a guest professorship, and the Royal Society for an Industry Fellowship. The Catalysis and Sensing for our Environment (CASE) consortium are thanked for networking opportunities.

语种：英文

外文关键词：unnatural alpha-amino acids; asymmetric catalysis; copper; conjugate addition; para-quinone methides

摘要：A highly efficient synthetic approach to unnatural chiral beta-Ar,Ar'-alpha-amino acid esters bearing two contiguous stereogenic centers has been developed. The first enantioselective 1,6-conjugate addition of glycine Schiff bases to para-quinone methides was achieved using a Cu(CH3CN)(4)BF4/Ph-Foxap catalytic system (1 mol %). The reaction proceeded smoothly to generate corresponding products in high yields with excellent diastereoselectivities (up to 99:1) and enantioselectivities (up to >99% ee). Subsequent reduction delivered enantiopure unnatural amino alcohols, which were utilized for the synthesis of novel chiral ligands.