Enantioselective ring opening of meso-epoxides by aromatic amines catalyzed by lanthanide iodo binaphtholates

被引：112

作者：

Carrée, F ^{[1
]}

Gil, R ^{[1
]}

Collin, J ^{[1
]}

机构：

[1] Univ Paris 11, ICMMO, UMR 8075, Lab Catalyse Mol, F-91405 Orsay, France

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 06期

关键词：

D O I：

10.1021/ol0475360

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lanthanide iodo binaphtholates are efficient enantioselective catalysts for the ring opening of meso-epoxides by various aromatic amines. The study of the influence of temperature on the ring opening of cyclohexene oxide by o-anisidine catalyzed by the samarium complex shows an isoinversion effect with the maximum enantiomeric excess at -40 C. Reactions of aniline, o-anisidine, or p=anisidine with five- or six-membered ring epoxides at this temperature allow the preparation of beta-amino alcohols with enantiomeric excesses up to 93%.

引用

页码：1023 / 1026

页数：4

共 53 条

[11] (R)-bis-binaphthoxy iodo lanthanides as catalysts for Diels-Alder reactions
Collin, J
Carrée, F
Giuseppone, N
Santos, I
[J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2003, 200 (1-2) : 185 - 189
[12] A regio- and stereoselective synthesis of beta-amino alcohols
Fu, XL
Wu, SH
[J]. SYNTHETIC COMMUNICATIONS, 1997, 27 (10) : 1677 - 1683
[13] Tandem reactions catalyzed by lanthanide iodides. Part 2: Tandem iminoaldol-enolisation reactions
Gil, R
Eternot, M
Guillerez, MG
Collin, J
[J]. TETRAHEDRON, 2004, 60 (13) : 3085 - 3090
[14] Tandem Mukaiyama Michael-aldol reactions catalysed by samarium diiodide
Giuseppone, N
Collin, J
[J]. TETRAHEDRON, 2001, 57 (43) : 8989 - 8998
[15] Mukaiyama aldol and Michael reactions catalyzed by lanthanide iodides
Giuseppone, N
Van de Weghe, P
Mellah, M
Collin, J
[J]. TETRAHEDRON, 1998, 54 (43) : 13129 - 13148
[16] TEMPERATURE EFFECTS IN ASYMMETRIC DIHYDROXYLATION - EVIDENCE FOR A STEPWISE MECHANISM
GOBEL, T
SHARPLESS, KB
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (09): : 1329 - 1331
[17] The theoretical basis of the isoinversion principle
Gypser, A
Norrby, PO
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (05): : 939 - 943
[18] On the mechanism of asymmetric nucleophilic ring-opening of epoxides catalyzed by (salen)Cr-III complexes
Hansen, KB
Leighton, JL
Jacobsen, EN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (44) : 10924 - 10925
[19] Conditions for maxima and minima as inversion points in the temperature dependence of selection processes
Heller, D
Buschmann, H
Neumann, H
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (02): : 175 - 181
[20] Nonlinear temperature behavior of product ratios in selection processes
Heller, D
Buschmann, H
Scharf, HD
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (16): : 1852 - 1854

← 1 2 3 4 5 6 →