Epoxidation of 4-Alkylidenecyclopentenones: A Route to the 1-Oxaspiro[2.4]hept-6-en-5-one Framework

被引：2
作者：
Ahmar, Mohammed [1 ]
Thome, Stephane [1 ]
Cazes, Bernard [1 ]
机构：
[1] Univ Lyon 1, CNRS UMR ICBMS 5246, Lab COSMO, F-69622 Villeurbanne, France
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 36期
关键词：
Synthetic methods; Epoxidation; Spiro compounds; PAUSON-KHAND REACTION; RING-CLOSURE; ACID; CONSTRUCTION;
D O I：
10.1002/ejoc.201201030
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Thanks to their lack of polarity, the exocyclic double bonds of 4-alkylidenecyclopentenones 4 are selectively epoxidized by MCPBA to give spiroepoxycyclopentenones 7, which feature the nonclassical 1-oxaspiro[2.4]hept-6-en-5-one framework. Under acidic conditions, compounds 7 undergo ring-opening to afford 4-hydroxy-4-(1-hydroxyalkyl)cyclopentenones 10.
引用
收藏
页码：7093 / 7105
页数：13
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