Asymmetric synthesis of chromanones via N-heterocyclic carbene catalyzed intramolecular crossed-benzoin reactions

被引：61

作者：

Enders, Dieter ^{[1
]}

Niemeier, Oliver ^{[1
]}

Raabe, Gerhard ^{[1
]}

机构：

[1] Univ Aachen, Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

SYNLETT | 2006年 / 15期

关键词：

organocatalysis; N-heterocyclic carbenes; asymmetric; synthesis; benzoin reaction; chromanones;

D O I：

10.1055/s-2006-950403

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective synthesis of 3-hydroxy-4-chromanones bearing a quaternary stereocenter via an N-heterocyclic carbene catalyzed intramolecular crossed-benzoin reaction is described.

引用

页码：2431 / 2434

页数：4

共 51 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] The quest for stable carbenes [J].

Arduengo, AJ ;

Krafczyk, R .

CHEMIE IN UNSERER ZEIT, 1998, 32 (01) :6-14

[3] Catalytic multicomponent synthesis of highly substituted pyrroles utilizing a one-pot Sila-Stetter/Paal-Knorr strategy [J].

Bharadwaj, AR ;

Scheidt, KA .

ORGANIC LETTERS, 2004, 6 (14) :2465-2468

[4]

BOHLER P, 1967, TETRAHEDRON LETT, P3479

[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] Stable non-N-heterocyclic carbenes (non-NHC): recent progress [J].

Canac, Y ;

Soleilhavoup, M ;

Conejero, S ;

Bertrand, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (24) :3857-3865

[7] 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

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

Christmann, M .

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

[9]

Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO

[10]

2-V

← 1 2 3 4 5 6 →