Asymmetric intramolecular crossed-benzoin reactions by N-heterocyclic carbene catalysis

被引：248

作者：

Enders, D ^{[1
]}

Niemeier, O ^{[1
]}

Balensiefer, T ^{[1
]}

机构：

[1] RWTH Aachen Univ, Inst Organ Chem, D-52074 Aachen, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 09期

关键词：

asymmetric synthesis; benzoin reaction; heterocycles; homogeneous catalysis; N-heterocyclic carbenes;

D O I：

10.1002/anie.200503885

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Getting cross: Excellent asymmetric inductions and very good yields are achieved in the generation of a quaternary stereocenter in α-hydroxy-substituted tetralones by using chiral N-heterocyclic carbene catalysts in an enantioselective intramolecular crossed-benzoin reaction. The synthesis of the corresponding α-hydroxyindanones with good ee values is also possible by this route. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：1463 / 1467

页数：5

共 41 条

[1] Synthesis and analysis of the sterically constrained L-glutamine analogues (3S,4R)-3,4-dimethyl-L-glutamine and (3S,4R)-3,4-dimethyl-L-pyroglutamic acid [J].

Acevedo, CM ;

Kogut, EF ;

Lipton, MA .

TETRAHEDRON, 2001, 57 (30) :6353-6359

[2] A STABLE CRYSTALLINE CARBENE [J].

ARDUENGO, AJ ;

HARLOW, RL ;

KLINE, M .

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

[3] The quest for stable carbenes [J].

Arduengo, AJ ;

Krafczyk, R .

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

[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]

Burstein C., 2004, ANGEW CHEM, V116, P6331

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

Christmann, M .

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

[8]

Christmann M., 2005, ANGEW CHEM, V117, P2688

[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 →