Enantio- and diastereoselective Darzens condensations

被引：24
作者：
Achard, Thierry J. R.
Belokon', Yuri N.
Ilyin, Michael
Moskalenko, Margarita
North, Michael
Pizzato, Francesca
机构：
[1] Univ Newcastle, Sch Nat Sci, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England
[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 17期
关键词：
D O I：
10.1016/j.tetlet.2007.03.009
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A cobalt(salen) complex has been shown to catalyse the asymmetric Darzens condensation between alpha-haloamides and aldehydes, allowing both the relative and absolute stereochemistry of the epoxy-amide products to be controlled. Under optimal conditions, cis-epoxides can be obtained diastereoselectively with up to 50%, enantiomeric excess, whilst by changing the leaving group and base, trans-epoxides can be produced diastereoselectively with up to 43% enantiomeric excess. (c) 2007 Elsevier Ltd. All rights reserved.
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页码：2965 / 2969
页数：5
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