1,3-dipolar cycle additions catalyzed by bis(oxazoline)-magnesium-based chiral complexes. The importance of a Mg(II) counterion

被引：65

作者：

Desimoni, G ^{[1
]}

Faita, G ^{[1
]}

Mortoni, A ^{[1
]}

Righetti, P ^{[1
]}

机构：

[1] Univ Pavia, Dipartimento Chim Organ, I-27100 Pavia, Italy

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 10期

关键词：

D O I：

10.1016/S0040-4039(99)00101-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 1,3-dipolar cycloaddition between N-acryloyl-oxazolidinone and diphenyl nitrone is catalyzed by chiral catalysts derived from bis(oxazoline) (R)-7 and Mg(II) perchlorate or triflate. In addition to complete regioselectivity, the endo cycloadduct can be obtained with up to 86% ee. The stereochemical results are due either to the specific counterion or to the presence of molecular sieves (as well as to the relative reagent concentrations). As a consequence, the enantioselectivity is opposite to that induced by the catalyst derived from Mg(II) iodide with the same chiral ligand. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2001 / 2004

页数：4

共 18 条

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