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螯合控制的分子间烯烃和炔烃氢酰化反应:β-硫代缩醛醛的效用

Chelation-controlled intermolecular alkene and alkyne hydroacylation: the utility of beta-thioacetal aldehydes.

作者信息

Willis Michael C, Randell-Sly Helen E, Woodward Robert L, Currie Gordon S

机构信息

Department of Chemistry, University of Bath, Bath, BA2 7AY, UK.

出版信息

Org Lett. 2005 May 26;7(11):2249-51. doi: 10.1021/ol050638l.

DOI:10.1021/ol050638l
PMID:15901181
Abstract

[reaction: see text]. Beta-thioacetal-substituted aldehydes, which are conveniently prepared from the corresponding ynals, can be combined with a range of alkynes or electron-poor alkenes to deliver intermolecular hydroacylation adducts. The reactions employ [Rh(dppe)]ClO4 as a catalyst and are proposed to proceed via a chelated rhodium acyl intermediate. The thioacetal-containing products can be deprotected to the corresponding ketones or reduced to alkanes in good yields.

摘要

[反应:见正文]。可方便地由相应的烯炔醛制备的β-硫代缩醛取代醛,能与一系列炔烃或贫电子烯烃反应生成分子间氢酰化加合物。这些反应使用[Rh(dppe)]ClO4作为催化剂,推测反应通过螯合铑酰基中间体进行。含硫代缩醛的产物可脱保护得到相应的酮,或高产率还原为烷烃。

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