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.
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页码：2363 / 2372
页数：10
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