Microwave-assisted ethylene-alkyne cross-metathesis:: synthesis of chiral 2-(N-1-acetyl-1-arylmethyl)-1,3-butadienes

被引：27
作者：
Castagnolo, D [1 ]
Renzulli, ML [1 ]
Galletti, E [1 ]
Corelli, F [1 ]
Botta, M [1 ]
机构：
[1] Univ Siena, Dipartimento Farmaco Chim Tecnol, I-53100 Siena, Italy
来源：
TETRAHEDRON-ASYMMETRY | 2005年 / 16卷 / 17期
关键词：
D O I：
10.1016/j.tetasy.2005.08.002
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Chiral 1-arylpropargyl amides, which are resistant to undergoing ethylene-alkyne cross-metathesis at atmospheric pressure, were reacted under microwave irradiation to afford enantiomerically enriched 2-(N-1-acetyl-1-arylmethyl)-1,3-butadienes within a few minutes. Enantiomerically enriched amides underwent ethylene-alkyne cross-metathesis with retention of configuration at the propargylic/allylic position. A series of chiral 2-(N-1-acetyl-1-arylmethyl)-1,3-butadienes were synthesised with ee >= 95%; these latter compounds could be used as building blocks for the synthesis of new antifungal and antiaromatase agents. (c) 2005 Elsevier Ltd. All rights reserved.
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页码：2893 / 2896
页数：4
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