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

[41] Solvent-free 1,6-conjugate arylation of para-quinone methides: A greener approach to unsymmetrical triarylmethanes
Hu, Yu
Tang, Min
Chen, Jia-Xuan
Wei, Shi-Qian
Tian, Yi
Zhang, Liang-Dong
Liu, Zhang-Qin
JOURNAL OF SAUDI CHEMICAL SOCIETY, 2021, 25 (09)
[42] para-Quinone Methides as Acceptors in 1,6-Nucleophilic Conjugate Addition Reactions for the Synthesis of Structurally Diverse Molecules
Lima, Carolina G. S.
Pauli, Fernanda P.
Costa, Dora C. S.
de Souza, Acacio S.
Forezi, Luana S. M.
Ferreira, Vitor F.
da Silva, Fernando de Silva
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (18) : 2650 - 2692
[43] Metal-Free, Acid-Catalyzed 1,6-Conjugate Addition of NH-Sulfoximines to para-Quinone Methides: Accessing to Diarylmethine Imino Sulfanone
More, Satish G.
Rupanawar, Bapurao D.
Suryavanshi, Gurunath
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (15): : 10129 - 10139
[44] Bismuth Triflate-Catalyzed Vinylogous Nucleophilic 1,6-Conjugate Addition of para-Quinone Methides with 3-Propenyl-2-silyloxyindoles
Xie, Kai-Xue
Zhang, Zhi-Pei
Li, Xin
ORGANIC LETTERS, 2017, 19 (24) : 6708 - 6711
[45] Metal-Free Regioselective 1,6-Conjugate Addition of Sulfide to para-Quinone Methides: Simple Access to E-Selective Thiaoxacyclophanes
Kotha, Sambasivarao
Gupta, Naveen K.
Solanke, Balaji U.
CHEMISTRYSELECT, 2023, 8 (34):
[46] 1,6-Conjugate Addition of 1,3-Dicarbonyl Compounds to para-Quinone Methides Enabled by Noncovalent N-Heterocyclic Carbene Catalysis
Santra, Surojit
Porey, Arka
Guin, Joyram
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (02) : 477 - 486
[47] Acetic Acid-Catalyzed 1,6-Addition of Indolizine to para-Quinone Methides
Lafzi, Ferruh
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (07)
[48] Photocatalytic Synthesis of Diarylmethyl Silanes via 1,6-Conjugate Addition of Silyl Radicals to p-Quinone Methides
Luo, Cong
Lu, Wen-hua
Wang, Guo-qin
Zhang, Zheng-bing
Li, Hai-qiong
Han, Pan
Yang, Dan
Jing, Lin-hai
Wang, Chen
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (05): : 3567 - 3576
[49] Synthesis of spiro[2.5]octa-4,7-dien-6-one with consecutive quaternary centers via 1,6-conjugate addition induced dearomatization of para-quinone methides
Gai, Kuo
Fang, Xinxin
Li, Xuanyi
Xu, Jinyi
Wu, Xiaoming
Lin, Aijun
Yao, Hequan
CHEMICAL COMMUNICATIONS, 2015, 51 (87) : 15831 - 15834
[50] TBAB-catalyzed 1,6-conjugate diazotization of para-quinone methides: A very effective access to polysubstituted α-diazocarbonyl compounds
Liu, Zhang-Qin
Liu, Sheng-Shu
Guan, Xiao-Yu
JOURNAL OF SAUDI CHEMICAL SOCIETY, 2024, 28 (03)

← 1 2 3 4 5 →