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

页码：5655 / 5662

页数：8

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