Rhodium-catalyzed asymmetric hydrogenation of β-branched enamides for the synthesis of β-stereogenic amines

被引：34

作者：

Zhang, Jian ^{[1
]}

Liu, Chong ^{[2
]}

Wang, Xingguang ^{[2
]}

Chen, Jianzhong ^{[2
]}

Zhang, Zhenfeng ^{[1
]}

Zhang, Wanbin ^{[1
,2
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Pharm, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China

[2] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, 800 Dongchuan Rd, Shanghai 200240, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 47期

基金：

中国国家自然科学基金;

关键词：

HIGHLY ENANTIOSELECTIVE HYDROGENATION; DYNAMIC KINETIC RESOLUTION; ALPHA-DEHYDROAMINO KETONES; FRIEDEL-CRAFTS ALKYLATION; BETA; BETA-DISUBSTITUTED NITROALKENES; PHOSPHORAMIDITE LIGANDS; EFFICIENT SYNTHESIS; BETA(2)-AMINO ACID; SPIRO DIPHOSPHINES; PRIMARY ALCOHOLS;

D O I：

10.1039/c8cc02798f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Using a rhodiumcomplex of a bisphosphine ligand (R)-SDP, beta-branched simple enamides with a (Z)-configuration were hydrogenated to beta-stereogenic amines in quantitative yields and with excellent enantioselectivities (88-96% ee).

引用

页码：6024 / 6027

页数：4

共 50 条

[21] Rhodium-Catalyzed Asymmetric Hydrogenation and Transfer Hydrogenation of α-Nitro Ketones
Sun, Hao
Xu, Liren
Ruan, Sai
Ratovelomanana-Vidal, Virginie
Chen, Gen-Qiang
Zhang, Xumu
ORGANIC LETTERS, 2024, 26 (46) : 10008 - 10012
[22] Rhodium-catalyzed asymmetric synthesis of silicon-stereogenic silicon-bridged arylpyridinones
Shintani, Ryo
Takano, Ryo
Nozaki, Kyoko
CHEMICAL SCIENCE, 2016, 7 (02) : 1205 - 1211
[23] Attraction versus Repulsion in Rhodium-Catalyzed Asymmetric Hydrogenation
Gridnev, Ilya D.
CHEMCATCHEM, 2016, 8 (22) : 3463 - 3465
[24] Rhodium-Catalyzed Homogeneous Asymmetric Hydrogenation of Naphthol Derivatives
Zhang, Shu-Xin
Long, Linhong
Li, Zeyu
He, Yan-Mei
Li, Shan
Chen, Hui
Hao, Wei
Fan, Qing-Hua
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2025, 147 (06) : 5197 - 5211
[25] MECHANISTIC STUDIES OF RHODIUM-CATALYZED ASYMMETRIC HOMOGENEOUS HYDROGENATION
BROWN, JM
CHALONER, PA
PARKER, D
ADVANCES IN CHEMISTRY SERIES, 1982, (196): : 355 - 369
[26] Rhodium-catalyzed asymmetric hydrogenation of unprotected β-enamine phosphonates
Zhou, Ming
Xue, Zejian
Cao, Min
Dong, Xiu-Qin
Zhang, Xumu
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (20) : 4582 - 4584
[27] Enantioselective Rhodium-Catalyzed Synthesis of Branched Allylic Amines by Intermolecular Hydroamination of Terminal Allenes
Cooke, Michael L.
Xu, Kun
Breit, Bernhard
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (43) : 10876 - 10879
[28] Asymmetric synthesis of diarylmethyl amines by rhodium-catalyzed asymmetric addition of aryl titanium reagents to imines
Hayashi, T
Kawai, M
Tokunaga, N
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) : 6125 - 6128
[29] Development of virtual ligand screening methods for asymmetric, rhodium-catalyzed hydrogenations of enamides
Donoghue, Patrick J.
Wiest, Olaf
Norrby, Per Ola
Helquist, Paul
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
[30] Asymmetric Rhodium-Catalyzed Addition of Thiols to Allenes: Synthesis of Branched Allylic Thioethers and Sulfones
Pritzius, Adrian B.
Breit, Bernhard
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (10) : 3121 - 3125

← 1 2 3 4 5 →