Enantioselective Synthesis of β-Substituted Cyclic Ketones via Cobalt-Catalyzed Asymmetric Reductive Coupling of Alkynes with Alkenes

被引：78

作者：

Wei, Chu-Hung ^{[1
]}

Mannathan, Subramaniyan ^{[1
]}

Cheng, Chien-Hong ^{[1
]}

机构：

[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 18期

关键词：

C BOND FORMATION; ALLYLIC ALCOHOLS; ATOM ECONOMY; ACTIVATED ALKENES; IMINE VINYLATION; IDEAL SYNTHESIS; HYDROGENATION; CYCLIZATION; ALDEHYDES; 1,3-ENYNES;

D O I：

10.1021/ja201827j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A CoI2/(R)-BINAP, Zn, ZnI2, H2O system efficiently catalyzes the intermolecular asymmetric reductive coupling of alkynes with cyclic enones to afford highly regio- and enantioselective beta-alkenyl cyclic ketones. A possible mechanism that involves the formation of a cobaltacyclopentene intermediate from the alkyne and cyclic enone is proposed.

引用

页码：6942 / 6944

页数：3

共 49 条

[1] Cobalt-catalyzed reductive coupling of activated alkenes with alkynes [J].

Chang, Hong-Tai ;

Jayanth, Thiruvellore Thatai ;

Wang, Chun-Chih ;

Cheng, Chien-Hong .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (39) :12032-12041

[2] Cobalt-catalyzed diastereoselective reductive [3+2] cycloaddition of allenes and enones [J].

Chang, Hong-Tai ;

Jayanth, Thiruvellore Thatai ;

Cheng, Chien-Hong .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (14) :4166-+

[3] New N-heterocyclic carbene ligand and its application in asymmetric nickel-catalyzed aldehyde/alkyne reductive couplings [J].

Chaulagain, Mani Raj ;

Sormunen, Grant J. ;

Montgomery, John .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (31) :9568-+

[4] Diverse reactivity manifolds of alkynyl enone- and alkynyl enal-derived nickelacycles: Discovery of nickel-promoted [3+2] and [2+1] cycloadditions [J].

Chowdhury, SK ;

Amarasinghe, KKD ;

Heeg, MJ ;

Montgomery, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (28) :6775-6776

[5] Highly chemoselective and stereoselective synthesis of Z-enol silanes [J].

Herath, Ananda ;

Montgomery, John .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (26) :8132-+

[6] Fully intermolecular nickel-catalyzed three-component couplings via internal redox [J].

Herath, Ananda ;

Li, Wei ;

Montgomery, John .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (02) :469-+

[7] Cobalt-catalyzed Alder-ene reaction [J].

Hilt, Gerhard ;

Treutwein, Jonas .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (44) :8500-8502

[8] Enantioselective reductive coupling of 1,3-enynes to glyoxalates mediated by hydrogen:: Asymmetric synthesis of β,γ-unsaturated α-hydroxy esters [J].

Hong, Young-Taek ;

Cho, Chang-Woo ;

Skucas, Eduardas ;

Krische, Michael J. .

ORGANIC LETTERS, 2007, 9 (19) :3745-3748

[9] Nickel-catalyzed intermolecular domino reactions [J].

Ikeda, S .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (08) :511-519

[10] Nickel-catalyzed coupling of carbonyl compounds and Alkynes or 1,3-dienes: An efficient method for the preparation of allylic, homoallylic, and bishomoallylic alcohols [J].

Ikeda, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (42) :5120-5122

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