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

[11] Nickel-catalyzed asymmetric multiple-component tandem coupling. Effects of simple monodentate oxazolines as chiral ligands [J].

Ikeda, S ;

Cui, DM ;

Sato, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (19) :4712-4713

[12] Enantioselective reductive cyclization of 1,6-enynes via rhodium-catalyzed asymmetric hydrogenation: C-C bond formation precedes hydrogen activation [J].

Jang, HY ;

Hughes, FW ;

Gong, HG ;

Zhang, JM ;

Brodbelt, JS ;

Krische, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (17) :6174-6175

[13] Rhodium-catalyzed reductive cyclization of 1,6-diynes and 1,6-enynes mediated by hydrogen: Catalytic C-C bond formation via capture of hydrogenation intermediates [J].

Jang, HY ;

Krische, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (25) :7875-7880

[14] Cobalt- and Nickel-Catalyzed Regio- and Stereoselective Reductive Coupling of Alkynes, Allenes, and Alkenes with Alkenes [J].

Jeganmohan, Masilamani ;

Cheng, Chien-Hong .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (35) :10876-10886

[15] Cobalt-Catalyzed Addition Reaction of Organoboronic Acids with Aldehydes: Highly Enantioselective Synthesis of Diarylmethanols [J].

Karthikeyan, Jaganathan ;

Jeganmohan, Masilamani ;

Cheng, Chien-Hong .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (30) :8989-8992

[16] Highly enantioselective direct reductive coupling of conjugated alkynes and α-ketoesters via rhodium-catalyzed asymmetric hydrogenation [J].

Kong, JR ;

Ngai, MY ;

Krische, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (03) :718-719

[17] DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF 6-MEMBERED-RING KETONES BY C-13 NMR [J].

LEMIERE, GL ;

DOMMISSE, RA ;

LEPOIVRE, JA ;

ALDERWEIRELDT, FC ;

HIEMSTRA, H ;

WYNBERG, H ;

JONES, JB ;

TOONE, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (05) :1363-1370

[18] Evolution of Efficient Strategies for Enone-Alkyne and Enal-Alkyne Reductive Couplings [J].

Li, Wei ;

Herath, Ananda ;

Montgomery, John .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (46) :17024-17029

[19] Cobalt-catalyzed regio- and stereoselective intermolecular enyne coupling: an efficient route to 1,3-diene derivatives [J].

Mannathan, Subramaniyan ;

Cheng, Chien-Hong .

CHEMICAL COMMUNICATIONS, 2010, 46 (11) :1923-1925

[20] Highly regioselective, catalytic asymmetric reductive coupling of 1,3-enynes and ketones [J].

Miller, KM ;

Jamison, TF .

ORGANIC LETTERS, 2005, 7 (14) :3077-3080

← 1 2 3 4 5 →