Catalytic Asymmetric Reductive Acyl Cross-Coupling: Synthesis of Enantioenriched Acyclic α,α-Disubstituted Ketones

被引：321

作者：

Cherney, Alan H. ^{[1
]}

Kadunce, Nathaniel T. ^{[1
]}

Reisman, Sarah E. ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 20期

基金：

美国国家科学基金会;

关键词：

ENANTIOSELECTIVE ALPHA-ARYLATION; UNACTIVATED ALKYL-HALIDES; CARBON BOND FORMATION; ALLYLIC ALKYLATION; ARYL HALIDES; CONJUGATE ADDITION; ORGANIC HALIDES; ACID-CHLORIDES; PALLADIUM; COMPLEXES;

D O I：

10.1021/ja402922w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first enantioselective Ni-catalyzed reductive acyl cross-coupling has been developed. Treatment of acid chlorides and racemic secondary benzyl chlorides with a Ni-II/bis(oxazoline) catalyst in the presence of Mn-0 as a stoichiometric reductant generates acyclic alpha,alpha-disubstituted ketones in good yields and high enantioselectivity without requiring stoichiometric chiral auxiliaries or pregeneration of organometallic reagents. The mild, base-free reaction conditions are tolerant of a variety of functional groups on both coupling partners.

引用

页码：7442 / 7445

页数：4

共 50 条

[41] Direct Catalytic Asymmetric Reductive Amination of Aliphatic Ketones Utilizing Diphenylmethanamine as Coupling Partner
Huang, Haizhou
Zhao, Yunfei
Yang, Yang
Zhou, Le
Chang, Mingxin
ORGANIC LETTERS, 2017, 19 (08) : 1942 - 1945
[42] Highly regioselective, catalytic asymmetric reductive coupling of 1,3-enynes and ketones
Miller, KM
Jamison, TF
ORGANIC LETTERS, 2005, 7 (14) : 3077 - 3080
[43] Applications of conjunctive cross-coupling towards the synthesis of β-hydroxy ketones
Law, Chunyin
Meng, Yan
Koo, Seung
Morken, James
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
[44] Catalytic asymmetric synthesis of enantioenriched cyclopropylmethanols.
Charette, AB
Molinaro, C
Brochu, C
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 : U50 - U50
[45] Reductive Cross-Coupling of Unreactive Electrophiles
Pang, Xiaobo
Su, Pei-Feng
Shu, Xing-Zhong
ACCOUNTS OF CHEMICAL RESEARCH, 2022, 55 (17) : 2491 - 2509
[46] Reductive Cross-Coupling of Vinyl Electrophiles
Pang, Xiaobo
Peng, Xuejing
Shu, Xing-Zhong
SYNTHESIS-STUTTGART, 2020, 52 (24): : 3751 - 3763
[47] Silver(I)-Catalyzed Reductive Cross-Coupling of Aldehydes to Structurally Diverse Cyclic and Acyclic Ethers
Liang, Ting
Dong, Guichao
Li, Chuang
Xu, Xin
Xu, Zhou
ORGANIC LETTERS, 2022, 24 (09) : 1817 - 1821
[48] A Concise Enantioselective Synthesis of ( S )-Preclamol via Asymmetric Catalytic Negishi Cross-Coupling Reaction
Zhou, Yun
Liu, Chunxiao
Wang, Lifeng
Han, Leng
Hou, Shicong
Bian, Qinghua
Zhong, Jiangchun
SYNLETT, 2019, 30 (07) : 860 - 862
[49] Synthesis of Acyl Alkenylindium Reagents and Their Application in the Synthesis of (Z)-α,β-Unsaturated Ketones via Palladium-atalyzed Cross-Coupling Reaction
Park, Youngchul
Min, Jiae
Eom, Dahan
Lee, Phil Ho
ORGANIC LETTERS, 2015, 17 (15) : 3934 - 3937
[50] Configurationally stable, enantioenriched organometallic nucleophiles in stereospecific Pd-catalyzed cross-coupling reactions: an alternative approach to asymmetric synthesis
Wang, Chao-Yuan
Derosa, Joseph
Biscoe, Mark R.
CHEMICAL SCIENCE, 2015, 6 (09) : 5105 - 5113

← 1 2 3 4 5 →