N-heterocyclic carbene catalyzed Aza-Morita-Baylis-Hillman reaction of cyclic enones with N-tosylarylimines

被引：110

作者：

He, Lin ^{[1
]}

Jian, Teng-Yue ^{[1
]}

Ye, Song ^{[1
]}

机构：

[1] Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, Beijing 100080, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 19期

关键词：

D O I：

10.1021/jo071247i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] N-Heterocyclic carbenes (NHCs) prove to be efficient catalysts for the aza-Morita-B aylis -Hillman (aza-MBH) reaction of cyclopent-2-en-1-one or cyclohex-2-en-1-one with a variety of N-tosylarylimines to give the aza-MBH adduct in high yields. Crossover experiments show NHC can add to N-tosylarylimines in a reversible manner, which allows the addition of NHC to cyclic enones and thus catalyzes the aza-Mortia- Baylis -Hillman reaction.

引用

页码：7466 / 7468

页数：3

共 39 条

[1] A STABLE CRYSTALLINE CARBENE [J].

ARDUENGO, AJ ;

HARLOW, RL ;

KLINE, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363

[2] Imidazolylidenes, imidazolinylidenes and imidazolidines [J].

Arduengo, AJ ;

Krafczyk, R ;

Schmutzler, R ;

Craig, HA ;

Goerlich, JR ;

Marshall, WJ ;

Unverzagt, M .

TETRAHEDRON, 1999, 55 (51) :14523-14534

[3] Recent advances in the Baylis-Hillman reaction and applications [J].

Basavaiah, D ;

Rao, AJ ;

Satyanarayana, T .

CHEMICAL REVIEWS, 2003, 103 (03) :811-891

[4] ON THE MECHANISM OF THIAMINE ACTION .4. EVIDENCE FROM STUDIES ON MODEL SYSTEMS [J].

BRESLOW, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (14) :3719-3726

[5] Organocatalyzed conjugate umpolung of α,β-unsaturated aldehydes for the synthesis of γ-butyrolactones [J].

Burstein, C ;

Glorius, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) :6205-6208

[6] Chiral N-heterocyclic carbenes as stereodirecting ligands in asymmetric catalysis [J].

César, V ;

Bellemin-Laponnaz, S ;

Gade, LH .

CHEMICAL SOCIETY REVIEWS, 2004, 33 (09) :619-636

[7] Highly stereoselective formal [3+3] cycloaddition of enals and azomethine imines catalyzed by N-heterocyclic carbenes [J].

Chan, Audrey ;

Scheidt, Karl A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (17) :5334-+

[8] Heterocycles derived from heteroatom-substituted carbenes [J].

Cheng, Y ;

Meth-Cohn, O .

CHEMICAL REVIEWS, 2004, 104 (05) :2507-2530

[9] Enantioselective, cyclopentene-forming annulations via NHC-catalyzed benzoin-oxy-cope reactions [J].

Chiang, Pei-Chen ;

Kaeobamrung, Juthanat ;

Bode, Jeffrey W. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (12) :3520-+

[10] Catalytic generation of activated carboxylates:: Direct, stereoselective synthesis of β-hydroxyesters from epoxyaldehydes [J].

Chow, KYK ;

Bode, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (26) :8126-8127

← 1 2 3 4 →