Synthesis of D-mannose-based azacrown ethers and their application in enantioselective reactions

被引：66

作者：

Bakó, P

Makó, A

Keglevich, G

Kubinyi, M

Pál, K

机构：

[1] Budapest Univ Technol & Econ, Dept Organ Chem Technol, H-1521 Budapest, Hungary

[2] Budapest Univ Technol & Econ, Dept Phys Chem, H-1521 Budapest, Hungary

[3] Hungarian Acad Sci, Inst Chem, Chem Res Ctr, H-1525 Budapest, Hungary

来源：

TETRAHEDRON-ASYMMETRY | 2005年 / 16卷 / 10期

关键词：

D O I：

10.1016/j.tetasy.2005.03.025

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

New chiral monoaza-15-crown-5 compounds anellated to methyl-4,6-O-benzylidene-alpha-D-mannopyranosides 2a-f have been synthesized. These crown ethers showed significant asymmetric induction as phase-transfer catalysts in the Michael addition of 2-nitropropane to chalcone (92% ee), in the Darzens condensation of phenacyl chloride with benzaldehyde (45% ee) and in the epoxidation of chalcones with tert-butyl-hydroperoxide (82%(, ee). The enantioselectivity was effected by the substituents at the nitrogen atom of the crown ring. The absolute configurations of epoxyketones 10 were determined by CD spectroscopy. (C) 2005 Elsevier Ltd. All rights reserved.

引用

页码：1861 / 1871

页数：11

共 49 条

[1] Improved procedure for Julia-Colonna asymmetric epoxidation of α,β-unsaturated ketones:: total synthesis of diltiazem and Taxol™ side-chain [J].