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

被引：249

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
Acevedo, CM
Kogut, EF
Lipton, MA
[J]. TETRAHEDRON, 2001, 57 (30) : 6353 - 6359
[2] A STABLE CRYSTALLINE CARBENE
ARDUENGO, AJ
HARLOW, RL
KLINE, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) : 361 - 363
[3] The quest for stable carbenes
Arduengo, AJ
Krafczyk, R
[J]. CHEMIE IN UNSERER ZEIT, 1998, 32 (01) : 6 - 14
[4] ON THE MECHANISM OF THIAMINE ACTION .4. EVIDENCE FROM STUDIES ON MODEL SYSTEMS
BRESLOW, R
[J]. 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
Burstein, C
Glorius, F
[J]. 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
Christmann, M
[J]. 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 →