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

共 50 条

[21] Catalyst-free 1,6-Conjugate Addition of S-Nucleophiles to para-Quinone Methides
Xie, Lei
Zang, Xuyang
Liu, Wanxing
Wu, Ping
Wang, Zhaoxue
Zhao, Chenyi
Gao, Zhenzhen
Li, Xiaojing
Nie, Shaozhen
Wu, Lingang
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (12)
[22] Halogen Bond Assisted Light Responsiveness of Para-Quinone Methides for 1,6-Conjugate Addition Reactions
Kumar, Sunil
Justin Thomas, K.R.
ChemCatChem, 2024, 16 (23)
[23] Asymmetric Catalytic 1,6-Conjugate Addition/Aromatization of para-Quinone Methides: Enantioselective Introduction of Functionalized Diarylmethine Stereogenic Centers
Chu, Wen-Dao
Zhang, Le-Fen
Bao, Xu
Zhao, Xian-He
Zeng, Chao
Du, Ji-Yuan
Zhang, Guo-Biao
Wang, Fang-Xin
Ma, Xiao-Yan
Fan, Chun-An
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) : 9229 - 9233
[24] 1,6-Conjugate addition of zinc alkyls to para-quinone methides in a continuous-flow microreactor
Jadhav, Abhijeet S.
Anand, Ramasamy Vijaya
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (01) : 56 - 60
[25] Decarboxylative 1,6-Conjugate Addition of α-Keto Acids with Para-Quinone Methides Enabled by Photoredox Catalysis
Wu Zijun
Wang Jian
ACTA CHIMICA SINICA, 2017, 75 (01) : 74 - 79
[26] Diastereoselective 1,6-Addition of α-Phosphonyloxy Enolates to para-Quinone Methides
Ali, Amjad
Jajoria, Raveena
Harit, Harish K.
Singh, Ravi P.
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (08): : 5213 - 5228
[27] Enantioselective synthesis of triarylmethanes via organocatalytic transfer hydrogenation of para-quinone methides
Han, Zhengyu
Zang, Yu
Liu, Chang
Guo, Wengang
Huang, Hai
Sun, Jianwei
CHEMICAL COMMUNICATIONS, 2022, 58 (51) : 7128 - 7131
[28] Base-mediated 1,6-conjugate addition of the Seyferth-Gilbert reagent to para-quinone methides
Gupta, Ashis Kumar
Ahamad, Shakir
Vaishanv, Narendra Kumar
Kant, Ruchir
Mohanan, Kishor
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (25) : 4623 - 4627
[29] Copper-catalyzed asymmetric 1,6-conjugate addition of in situ generated para-quinone methides with β-ketoesters
Wang, Yi-Feng
Wang, Chao-Jie
Feng, Qing-Zhou
Zhai, Jing-Jing
Qi, Suo-Suo
Zhong, Ai-Guo
Chu, Ming-Ming
Xu, Dan-Qian
CHEMICAL COMMUNICATIONS, 2022, 58 (46) : 6653 - 6656
[30] Catalytic Asymmetric 1,6-Conjugate Addition of para-Quinone Methides: Formation of All-Carbon Quaternary Stereocenters
Wang, Zhaobin
Wong, Yuk Fai
Sun, Jianwei
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (46) : 13711 - 13714

← 1 2 3 4 5 →