Asymmetric synthesis using catalysts containing multiple stereogenic centres and a trans-1,2-diaminocyclohexane core;: reversal of predominant enantioselectivity upon N-alkylation

被引：27

作者：

Cobb, AJA ^{[1
]}

Marson, CM ^{[1
]}

机构：

[1] UCL, Dept Chem, Christopher Ingold Labs, London WC1H 0AJ, England

来源：

TETRAHEDRON | 2005年 / 61卷 / 05期

基金：

英国工程与自然科学研究理事会;

关键词：

amine ligands; catalysis; asymmetric synthesis; carbonyl alkylation; Michael addition;

D O I：

10.1016/j.tet.2004.11.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Methylation of ligands containing a trans-1,2-diaminocyclohexane core and multiple stereogenic centres is shown to provide the product of the opposite configuration in significant enantiomeric excess, in the addition of diethylzinc to aldehydes. Some of the ligands were effective in an asymmetric Michael addition. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：1269 / 1279

页数：11

共 32 条

[1] ENANTIOSELECTIVE ETHYLATION OF ALDEHYDES CATALYZED BY CHIRAL C-2-SYMMETRICAL BETA-HYDROXY-M-XYLYLENE DIAMINES
ANDRES, JM
MARTINEZ, MA
PEDROSA, R
PEREZENCABO, A
[J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (01) : 67 - 72
[2] Synthesis and stereochemistry of cobalt(III) complexes with the new optically active phosphine ligand, N,N'-bis[2-(diphenylphosphanyl)ethyl]-(1R,2R)-cyclohexane-1,2-diamine (ch-PNNP). Crystal structure of Lambda-cis beta-[Co(acac)(ch-PNNP)](ClO4)(2)
Atoh, M
Sorensen, HO
Andersen, P
[J]. ACTA CHEMICA SCANDINAVICA, 1997, 51 (12): : 1169 - 1177
[3] trans-1,2-diaminocyclohexane derivatives as chiral reagents, scaffolds, and ligands for catalysis: Applications in asymmetric synthesis and molecular recognition
Bennani, YL
Hanessian, S
[J]. CHEMICAL REVIEWS, 1997, 97 (08) : 3161 - 3195
[4] BROWN HC, 1981, SYNTHESIS-STUTTGART, P996
[5] CANTARELLI G, 1970, FARMACO, P248
[6] Reversal of enantioselectivity using catalysts containing multiple stereogenic centres
Cobb, AJA
Marson, CM
[J]. TETRAHEDRON-ASYMMETRY, 2001, 12 (11) : 1547 - 1550
[7] ZINC-COMPLEXES OF CHIRAL PHENOLS AS CATALYSTS FOR ENANTIOSELECTIVE ADDITION OF ORGANOZINC REAGENTS TO ALDEHYDES
COREY, EJ
HANNON, FJ
[J]. TETRAHEDRON LETTERS, 1987, 28 (44) : 5237 - 5240
[8] Enantioselective addition of Et(2)Zn to aldehydes promoted by a chiral Schiff base metal complex
Cozzi, PG
Papa, A
UmaniRonchi, A
[J]. TETRAHEDRON LETTERS, 1996, 37 (26) : 4613 - 4616
[9] Metal complexes of new, chiral N2O2 tetradentate ligands
Cross, RJ
Farrugia, LJ
Newman, PD
Peacock, RD
Stirling, D
[J]. INORGANIC CHEMISTRY, 1999, 38 (06) : 1186 - 1192
[10] NEW BETA-AMINO ALCOHOLS DERIVED FROM L-VALINE AS CHIRAL INDUCTORS FOR ENANTIOSELECTIVE REDUCTIONS OF, AND NUCLEOPHILIC ADDITIONS TO CARBONYL-COMPOUNDS
DELAIR, P
EINHORN, C
EINHORN, J
LUCHE, JL
[J]. TETRAHEDRON, 1995, 51 (01) : 165 - 172

← 1 2 3 4 →