Aspects of stereocontrol in the L-Selectride reduction of 4-acyl-1,3-dioxolane derivatives

被引：15

作者：

Robertson, Jeremy ^{[1
]}

Unsworth, William P. ^{[1
]}

Lamont, Scott G. ^{[2
]}

机构：

[1] Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

[2] AstraZeneca Global R&D, Macclesfield SK10 4TG, Cheshire, England

来源：

TETRAHEDRON | 2010年 / 66卷 / 13期

基金：

英国工程与自然科学研究理事会;

关键词：

Diastereoselective; Ketones; Lactols; Polyols; 2,3-O-ISOPROPYLIDENE DERIVATIVES; MALAYAMYCIN-A; (+)-BULGECININE; NUCLEOPHILES; ANALOGS; ROUTE; ACIDS;

D O I：

10.1016/j.tet.2010.01.107

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The application of L-Selectride, either alone or in combination with ZnCl(2), to aryl ketones 1, 8 and 11 resulted in highly anti-stereoselective reduction. In contrast, lactols 22 and 23 gave a moderate syn-preference using L-Selectride alone and a high syn-preference in the presence Of ZnCl(2). Uniquely, high anti- stereoselectivity was observed in the reduction of o-anisyl lactol 37 with L-Selectride alone, which was switched to a high syn-preference when ZnCl(2) Was present. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：2363 / 2372

页数：10

共 36 条

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