The Prins Reaction Using Ketones: Rationalization and Application toward the Synthesis of the Portentol Skeleton

被引：40
|
作者：
Jacolot, Maiwenn [1 ]
Jean, Mickael [1 ]
Levoin, Nicolas [2 ]
van de Weghe, Pierre [1 ]
机构：
[1] Univ Rennes 1, UMR 6226, Equipe PNSCM, UFR Sci Biol & Pharmaceut, F-35043 Rennes, France
[2] Bioprojet Biotech, F-35762 St Gregoire, France
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 01期
关键词：
CYCLIZATION;
D O I：
10.1021/ol202829u
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report a TMSI-promoted Prins cyclization reaction with ketones as carbonyl partners to prepare polysubstituted chiral spirotetrahydropyrans. In the presence of racemic 2-methylcyclohexanone a dynamic kinetic resolution occurred affording one stereoisomer. The observed enantiospecificity has been rationalized by DFT calculation.
引用
收藏
页码：58 / 61
页数：4
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