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

页码：58 / 61

页数：4

共 23 条

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