Diastereoselective and Enantioselective Synthesis of Unsymmetric β,β-Diaryl-α-Amino Acid Esters via Organocatalytic 1,6-Conjugate Addition of para-Quinone Methides

被引：98
|
作者：
Zhang, Xiang-Zhi [1 ]
Deng, Yu-Hua [3 ]
Yan, Xu [1 ]
Yu, Ke-Yin [1 ]
Wang, Fang-Xin [1 ]
Ma, Xiao-Yan [1 ]
Fan, Chun-An [1 ,2 ]
机构：
[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, 222 Tianshui Nanlu, Lanzhou 730000, Peoples R China
[2] Peking Univ, State Key Lab Nat & Biomimet Drugs, 38 Xueyuan Lu, Beijing 100191, Peoples R China
[3] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 13期
基金：
中国国家自然科学基金;
关键词：
ALPHA-AMINO-ACIDS; BETA-SUBSTITUTED TRYPTOPHANS; PHASE-TRANSFER CATALYSIS; RING-OPENING REACTIONS; ASYMMETRIC-SYNTHESIS; EXPEDIENT ACCESS; ALKYLATION; SCALE; ADDITION/AROMATIZATION; DIPHENYLALANINE;
D O I：
10.1021/acs.joc.6b00390
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel strategy based on phase transfer catalysis for the diastereoselective and enantioselective direct assembly of unsymmetric beta,beta-diaryl-alpha-amino acid esters via 1,6-conjugate addition of para-quinone methides and glycine derivatives is described. This protocol also provides an alternative route to the synthetically interesting functionalized chiral tetrahydroisoquinoline and its analogues.
引用
收藏
页码：5655 / 5662
页数：8
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