Copper-catalyzed asymmetric Michael reactions with a-amino acid amides: Synthesis of an optically active piperidine derivative

被引：0

作者：

Christoffers, J ^{[1
]}

Scharl, H ^{[1
]}

机构：

[1] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 2002卷 / 09期

关键词：

asymmetric synthesis; catalysis; C-C coupling; copper; Michael additions;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Quaternary stereocenters are obtained at room temperature in copper-catalyzed asymmetric Michael reactions with alpha-amino acid amides as chiral auxiliaries. L-Valine diethylamide was applied as a chiral auxiliary, and an optically active piperidine derivative was prepared with 97% ee. The optical purity of the product was established by GLC after cyclization to a hexahydroisoquinolonecarboxylate. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

引用

页码：1505 / 1508

页数：4

共 50 条

[31] Copper-Catalyzed Oxidative Cross-Coupling Reactions for the Synthesis of β-Acyl-α-amino Acid Derivatives in Aqueous Medium
Zhou, Anxi
Zhou, Xiaofei
Mao, Liuliang
Zheng, Dagui
Zhu, Xianhong
Chen, Zongbao
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (04) : 1070 - 1078
[32] Copper-Catalyzed Asymmetric Formal [3+2] Cycloaddition of Propargylic Acetates with Hydrazines: Enantioselective Synthesis of Optically Active 2-Pyrazolines
Zhang, De-Yang
Shao, Long
Xu, Jie
Hu, Xiang-Ping
ACS CATALYSIS, 2015, 5 (09): : 5026 - 5030
[33] Copper-Catalyzed Asymmetric Michael Addition of Magnesium, Zinc, and Aluminum Organometallic Reagents: Efficient Synthesis of Chiral Molecules
Thaler, Tobias
Knochel, Paul
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (04) : 645 - 648
[34] ASYMMETRIC REACTIONS CATALYZED BY CHIRAL METAL-COMPLEXES .7. CATALYTIC ASYMMETRIC SYNTHESIS OF OPTICALLY-ACTIVE BETA-AMINO ACIDS
ACHIWA, K
SOGA, T
TETRAHEDRON LETTERS, 1978, (13) : 1119 - 1120
[35] Copper-catalyzed cross-coupling of imines, acid chlorides, and organostannanes:: A multicomponent synthesis of α-substituted amides
Black, DA
Arndtsen, BA
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (13): : 5133 - 5138
[36] Copper-catalyzed enantioselective Henry reactions of α-keto esters:: An easy entry to optically active β-nitro-α-hydroxy esters and β-amino-α-hydroxy esters
Christensen, C
Juhl, K
Hazell, RG
Jorgensen, KA
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14): : 4875 - 4881
[37] Novel thiolated amino-alcohols as chiral ligands for copper-catalyzed asymmetric nitro-aldol reactions
Mansawat, Woraluk
Saengswang, Ittiphol
U-prasitwong, Palita
Bhanthumnavin, Worawan
Vilaivan, Tirayut
TETRAHEDRON LETTERS, 2007, 48 (24) : 4235 - 4238
[38] Ligand-Enabled, Copper-Catalyzed Electrophilic Amination for the Asymmetric Synthesis of beta-Amino Acids
Tak, Raj K.
Noda, Hidetoshi
Shibasaki, Masakatsu
ORGANIC LETTERS, 2021, 23 (21) : 8617 - 8621
[39] Copper-Catalyzed Cross-Dehydrogenative-Coupling Reaction of N-Arylglycine Esters with Imides or Amides for Synthesis of α-Substituted α-Amino Acid Esters
Xiao, Li-Jin
Zhu, Zhi-Qiang
Guo, Dong
Xie, Zong-Bo
Lu, Yue
Le, Zhang-Gao
SYNLETT, 2018, 29 (12) : 1659 - 1663
[40] Asymmetric copper-catalyzed synthesis of α-amino boronate esters from N-tert-butanesulfinyl aldimines
Beenen, Melissa A.
An, Chihui
Ellman, Jonathan A.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (22) : 6910 - +

← 1 2 3 4 5 →