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丙二烯的黄金时代:金催化β-羟基丙二烯环异构化生成二氢吡喃。

Golden times for allenes: Gold-catalyzed cycloisomerization of beta-hydroxyallenes to dihydropyrans.

作者信息

Gockel Birgit, Krause Norbert

机构信息

Organic Chemistry II, Dortmund University, D-44221 Dortmund, Germany.

出版信息

Org Lett. 2006 Sep 28;8(20):4485-8. doi: 10.1021/ol061669z.

Abstract

The gold(I)-catalyzed 6-endo cycloisomerization of beta-hydroxyallenes provides a mild and efficient access to chiral functionalized dihydropyrans which were obtained at room temperature in good chemical yields with axis-to-center chirality transfer. The method was extended to the beta-aminoallene 12, which afforded tetrahydropyridine 13 in good yield as well.

摘要

金(I)催化的β-羟基丙二烯的6-内型环异构化反应提供了一种温和且高效的方法来合成手性官能化二氢吡喃,这些产物在室温下以良好的化学产率获得,且具有轴手性到中心手性的转移。该方法扩展到了β-氨基丙二烯12,它也能以良好的产率得到四氢吡啶13。

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