Highly diastereo- and enantioselective reactions of enecarbamates with ethyl glyoxylate to give optically active syn and anti α-alkyl-β-hydroxy imines and ketones

被引：65

作者：

Matsubara, R ^{[1
]}

Nakamura, Y ^{[1
]}

Kobayashi, S ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 25期

关键词：

asymmetric catalysis; aza-ene reaction; copper N ligands; synthetic methods;

D O I：

10.1002/anie.200460165

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The remarkably selective addition of enecarbamates 2 to ethyl glyoxylate (1) in the presence of a copper-dilmine catalyst (0.1 mol%) gives the corresponding imines 3 in high yields with excellent enantioselectivities. A concerted aza-enetype reaction mechanism was proposed to explain the stereochemical outcome.

引用

页码：3258 / 3260

页数：3

共 36 条

[1] THE ASYMMETRIC MICHAEL REACTION USING CHIRAL IMINES UNDER NEUTRAL CONDITIONS - STEREOCHEMICAL EVIDENCES IN SUPPORT OF A CYCLIC TRANSITION-STATE
AMBROISE, L
DESMAELE, D
MAHUTEAU, J
DANGELO, J
[J]. TETRAHEDRON LETTERS, 1994, 35 (52) : 9705 - 9708
[2] [Anonymous], [No title captured]
[3] ARREIRA EM, 1999, COMPREHENSIVE ASYMME, P998
[4] Transition states of amine-catalyzed aldol reactions involving enamine intermediates: Theoretical studies of mechanism, reactivity, and stereoselectivity
Bahmanyar, S
Houk, KN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (45) : 11273 - 11283
[5] Carreira E. M., 2000, MODERN CARBONYL CHEM, P227
[6] 1,3-SYN DIASTEREOSELECTIVE REDUCTION OF BETA-HYDROXYKETONES UTILIZING ALKOXYDIALKYLBORANES
CHEN, KM
HARDTMANN, GE
PRASAD, K
REPIC, O
SHAPIRO, MJ
[J]. TETRAHEDRON LETTERS, 1987, 28 (02) : 155 - 158
[7] AN EFFICIENT ROUTE TO AMINOANTHRAQUINONES AND DERIVATIVES VIA A DIELS-ALDER REACTION
CHIGR, M
FILLION, H
ROUGNY, A
[J]. TETRAHEDRON LETTERS, 1987, 28 (39) : 4529 - 4532
[8] Christoffers J, 2001, CHEM-EUR J, V7, P1014, DOI 10.1002/1521-3765(20010302)7:5<1014::AID-CHEM1014>3.0.CO
[9] 2-X
[10] THE ASYMMETRIC MICHAEL ADDITION-REACTIONS USING CHIRAL IMINES
DANGELO, J
DESMAELE, D
DUMAS, F
GUINGANT, A
[J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (04) : 459 - 505

← 1 2 3 4 →