Dimethyl 3-methylglutaconate:: a useful reagent for the diastereoselective synthesis of functionalized 5,6-dihydro-2H-pyran-2-ones

被引:9
作者
Audin, P [1 ]
Piveteau, N [1 ]
Dussert, AS [1 ]
Paris, J [1 ]
机构
[1] Fac Pharm Lyon, ISPB, Chim Therapeut Lab, F-69373 Lyon 08, France
关键词
D O I
10.1016/S0040-4020(99)00383-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Condensation of dimethyl 3-methylglutaconate with aldehydes leads to the formation of 6-substituted 5,6-dihydro-2H-pyran-2-ones through aldolisation followed by cyclization. The conditions of the aldolisation reaction in order to increase diastereoselectivity are described. Chiral aldehydes and aminoaldehydes have been used. The 6-substituted 5,6-dihydro-2H-pyran-2-ones prepared from aminoaldehydes could be interesting protease inhibitors. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7847 / 7858
页数:12
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