N-Heterocyclic Carbene-Catalyzed Hydroacylation of Unactivated Double Bonds

被引：189

作者：

Hirano, Keiichi ^{[1
]}

Biju, Akkattu T. ^{[1
]}

Piel, Isabel ^{[1
]}

Glorius, Frank ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 40期

关键词：

GAMMA-BUTYROLACTONES; CONJUGATE UMPOLUNG; DIRECT ANNULATIONS; BENZOIN REACTIONS; ALDEHYDES; ENALS; CYCLIZATION; MECHANISM; KETONES;

D O I：

10.1021/ja906361g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An intramolecular N-heterocyclic carbene (NHC)-catalyzed hydroacylation of unactivated double bonds is reported. Systematic variation of the catalyst structure revealed an N-mesitylthiazolylidene annulated with a seven-membered ring to be especially reactive. This NHC enables a unique C-C bond-forming reaction to afford substituted chroman-4-ones in moderate to excellent yields, even ones containing all-carbon quaternary centers.

引用

页码：14190 / +

页数：3

共 39 条

[1] 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

[2] 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

[3]

BURSTEIN C, 2006, SYNTHESIS-STUTTGART, P2413

[4] Hydroacylation of activated ketones catalyzed by N-heterocyclic carbenes [J].

Chan, A ;

Scheidt, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (14) :4558-4559

[5] New developments in the asymmetric Stetter reaction [J].

Christmann, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (18) :2632-2634

[6] Catalytic enantioselective Conia-ene reaction [J].

Corkey, BK ;

Toste, FD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (49) :17168-17169

[7] Rh-Catalyzed Intramolecular Olefin Hydroacylation: Enantioselective Synthesis of Seven- and Eight-Membered Heterocycles [J].

Coulter, Matthew M. ;

Dornan, Peter K. ;

Dong, Vy M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (20) :6932-+

[8] The Catalytic Asymmetric Intramolecular Stetter Reaction [J].

de Alaniz, Javier Read ;

Rovis, Tomislav .

SYNLETT, 2009, (08) :1189-1207

[9] N-Heterocyclic Carbenes in Late Transition Metal Catalysis [J].

Diez-Gonzalez, Silvia ;

Marion, Nicolas ;

Nolan, Steven P. .

CHEMICAL REVIEWS, 2009, 109 (08) :3612-3676

[10] Asymmetric intramolecular crossed-benzoin reactions by N-heterocyclic carbene catalysis [J].

Enders, D ;

Niemeier, O ;

Balensiefer, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (09) :1463-1467

← 1 2 3 4 →