Enantioselective Synthesis of Carbo- and Heterocycles through a CuH-Catalyzed Hydroalkylation Approach

被引：104

作者：

Wang, Yi-Ming ^{[1
]}

Bruno, Nicholas C. ^{[1
]}

Placeres, Angel L. ^{[1
]}

Zhu, Shaolin ^{[1
]}

Buchwald, Stephen L. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 33期

基金：

美国国家卫生研究院;

关键词：

C BOND FORMATION; ANTI-MARKOVNIKOV HYDROALKYLATION; ASYMMETRIC-SYNTHESIS; COPPER(I)-CATALYZED REACTION; VERSATILE CATALYSTS; ALKYL-GROUPS; ALKENES; HYDROAMINATION; ALCOHOLS; OLEFINS;

D O I：

10.1021/jacs.5b07061

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enantios elective, intramolecular hydro-alkylation of halide-tethered styrenes has been achieved through a copper hydride-catalyzed process. This approach allowed for the synthesis of enantioenriched cydobutanes, cyclopentanes, indanes, and six-membered N- and O-heterocycles. This protocol was applied to the synthesis of the commercial serotonin reuptake inhibitor (-)-paroxetine.

引用

页码：10524 / 10527

页数：4

共 50 条

[41] Recent advances in cascade radical cyclization of radical acceptors for the synthesis of carbo- and heterocycles
Liao, Jianhua
Yang, Xiao
Ouyang, Lu
Lai, Yinlong
Huang, Jiuzhong
Luo, Renshi
ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (06) : 1345 - 1363
[42] Multicomponent reactions of carbonyl compounds and derivatives of cyanoacetic acid: Synthesis of carbo- and heterocycles
Shestopalov, Anatoliy M.
Shestopalov, Alexander A.
Rodinovskaya, Lyudmila A.
SYNTHESIS-STUTTGART, 2008, (01): : 1 - 25
[43] CuH-Catalyzed Reductive Coupling of Nitroarenes with Phosphine Oxides for the Direct Synthesis of Phosphamides
Tang, Jie
Li, Zhiyou
Meng, Qi
Liu, Long
Huang, Tianzeng
Li, Chunya
Li, Qiang
Chen, Tieqiao
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (11): : 7848 - 7858
[44] CuH-Catalyzed Enantioselective Intramolecular Reductive Aldol Reactions Generating Three New Contiguous Asymmetric Stereocenters
Lipshutz, Bruce H.
Amorelli, Benjamin
Unger, John B.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (44) : 14378 - +
[45] CuH-Catalyzed Regio- and Enantioselective Hydrocarboxylation of Allenes: Toward Carboxylic Acids with Acyclic Quaternary Centers
Feng, Sheng
Buchwald, Stephen L.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (13) : 4935 - 4941
[46] CuH-catalyzed enantioselective intramolecular reductive aldol reactions generating three new contiguous asymmetric stereocenters
Lipshutz, Bruce H.
Amorelli, Benjamin
Unger, John B.
Journal of the American Chemical Society, 2008, 130 (44): : 14378 - 14379
[47] CuH-Catalyzed Regio- And Enantioselective Hydrocarboxylation of Allenes: Toward Carboxylic Acids with Acyclic Quaternary Centers
Feng, Sheng
Buchwald, Stephen L.
Journal of the American Chemical Society, 2021, 143 (13): : 4935 - 4941
[48] ORGN 633-Synthesis of carbo- and heterocycles via palladium-catalyzed intramolecular direct arylation of vinyl iodides
Kadnikov, Dmitry V.
Klisiewicz, Paul
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 236
[49] Efficient synthesis of α-substituted ethylphosphonates via CuH-catalyzed conjugate reduction of terminal alkenylphosphonate
Zhang, Li
Fang, Yewen
Jin, Xiaoping
Guo, Ting
Li, Ruifeng
Li, Yan
Li, Xie
Yang, Yi
Yuan, Meijuan
Tian, Zongming
TETRAHEDRON LETTERS, 2017, 58 (48) : 4538 - 4541
[50] Gold-Catalyzed Reactions Towards Diversity: From Simple Substrates to Functionalized Carbo- and Heterocycles
Michelet, Veronique
CHEMICAL RECORD, 2021, 21 (12): : 3884 - 3896

← 1 2 3 4 5 →