First anti-Selective Direct Michael Addition of α-Alkoxy Ketones to Enones by Cooperative Catalysis of Samarium(III) Trifluoromethanesulfonate and Tributyltin Methoxide

被引：2

作者：

Esumi, Naoto ^{[1
]}

Nishimoto, Yoshihiro ^{[2
]}

Yasuda, Makoto ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, 2-1 Yamada Oka, Suita, Osaka 5650871, Japan

[2] Osaka Univ, Grad Sch Engn, Frontier Res Base Global Young Researchers Ctr Op, 2-1 Yamada Oka, Suita, Osaka 5650871, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 19期

基金：

日本学术振兴会;

关键词：

Michael addition; Tin; Samarium; Methoxy ketones; Diastereoselectivity; CHIRAL PALLADIUM ENOLATE; LINKED-BINOL COMPLEX; ALPHA; BETA-UNSATURATED KETONES; 1,3-DICARBONYL COMPOUNDS; CONJUGATE ADDITIONS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC CATALYST; ALDOL CYCLIZATION; ESTERS; CONSTRUCTION;

D O I：

10.1002/ejoc.201700501

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new highly anti-diastereoselective Michael addition of alpha-alkoxy ketones to alpha,beta-unsaturated ketones was achieved. This method features a dual-catalyst protocol that combines samarium(III) trifluoromethanesulfonate and Bu3SnOMe. The combination of these two catalysts effectively allowed the generation of enolate species from alpha-alkoxy ketones and produced Michael adducts in high yields with high anti diastereoselectivity. A variety of enones and alpha-alkoxy ketones were applied to this system to give the anti products. One-pot domino Michael/aldol reactions effectively afforded cyclic enones with a defined configuration.

引用

页码：2831 / 2835

页数：5

共 61 条

[21] Direct generation of nucleophilic chiral palladium enolate from 1,3-dicarbonyl compounds: Catalytic enantioselective Michael reaction with enones [J].

Hamashima, Y ;

Hotta, D ;

Sodeoka, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (38) :11240-11241

[22] Direct catalytic asymmetric Michael reaction of hydroxyketones:: Asymmetric Zn catalysis with a Et2Zn/linked-BINOL complex [J].

Harada, S ;

Kumagai, N ;

Kinoshita, T ;

Matsunaga, S ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) :2582-2590

[23] ASYMMETRIC INDUCTION IN THE MICHAEL REACTION [J].

HERMANN, K ;

WYNBERG, H .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (13) :2238-2244

[24] A New Strategy for Enantioselective Construction of Multisubstituted Five-Membered Oxygen Heterocycles via a Domino Michael/Hemiketalization Reaction [J].

Hua, Yuan-Zhao ;

Liu, Meng-Meng ;

Huang, Pei-Jin ;

Song, Xixi ;

Wang, Min-Can ;

Chang, Jun-Biao .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (34) :11994-11998

[25] Highly enantioselective direct conjugate addition of ketones to nitroalkenes promoted by a chiral primary amine-thiourea catalyst [J].

Huang, Hongbing ;

Jacobsen, Eric N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (22) :7170-7171

[26] SYN-SELECTIVE MICHAEL ADDITION OF LITHIATED 2-ALKOXYACETATES AND 2-ALKOXYACETAMIDES TO ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS [J].

KANEMASA, S ;

NOMURA, M ;

WADA, E .

CHEMISTRY LETTERS, 1991, (10) :1735-1738

[27] Stable, storable, and reusable asymmetric catalyst: A novel La-linked-BINOL complex for the catalytic asymmetric Michael reaction [J].

Kim, YS ;

Matsunaga, S ;

Das, J ;

Sekine, A ;

Ohshima, T ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (27) :6506-6507

[28]

Krause N, 2001, SYNTHESIS-STUTTGART, P171

[29] Enantioselective 1,4-addition of unmodified ketone catalyzed by a bimetallic Zn-Zn-linked-BINOL complex [J].

Kumagai, N ;

Matsunaga, S ;

Shibasaki, M .

ORGANIC LETTERS, 2001, 3 (26) :4251-4254

[30]

Kundsen K. R., 2006, CHEM COMMUN, V66

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