Enantio-face control by molecular sieves in the asymmetric Diels-Alder reaction

被引：27

作者：

Moharram, SM

Hirai, G

Koyama, K

Oguri, H

Hirama, M ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

[2] Japan Sci & Technol Corp, JST, CREST, Sendai, Miyagi 9808578, Japan

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 34期

关键词：

asymmetric Diels-Alder reaction; molecular sieves 4 angstrom; chiral TADDOL-Ti complex;

D O I：

10.1016/S0040-4039(00)01116-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The presence of molecular sieves 4 Angstrom (MS 4 Angstrom) significantly influenced enantioselectivity in the Diels-Alder reaction of 2-methoxy-5-methyl-1,4-benzoquinone with 1-acetoxy-1,3-butadiene promoted by chiral TADDOL-Ti complexes. In the absence of MS 4 Angstrom the (R)-adduct was formed in 72% ee, and in the presence of MS 4 Angstrom the (S)-enantiomer in up to 53% ee. Capture of HCl by MS 4 Angstrom has been demonstrated to play a critical role. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：6669 / 6673

页数：5

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