氢过氧化物与氧杂环丁烷的分子内反应：1,2 - 二氧戊环和1,2 - 二氧六环的立体选择性合成
Intramolecular reactions of hydroperoxides and oxetanes: stereoselective synthesis of 1,2-dioxolanes and 1,2-dioxanes.
作者信息
Dai Peng, Dussault Patrick H
机构信息
Department of Chemistry, University of Nebraska-Lincoln, Lincoln, Nebraska 68588-0304, USA.
出版信息
Org Lett. 2005 Sep 29;7(20):4333-5. doi: 10.1021/ol051407h.
PMID:16178526
Abstract
[reactions: see text] The 5-exo openings of oxetanes by hydroperoxides proceed rapidly and stereospecifically to furnish 1,2-dioxolanes. The corresponding 6-exo cyclizations are slower and proceed with moderate stereoselectivity. In the case of hydroperoxy acetals, 5-exo nucleophilic transfer of alkoxide competes effectively with 6-exo attack by the hydroperoxide.
摘要
[反应：见正文] 氢过氧化物使氧杂环丁烷发生5-外向开环反应迅速且具有立体专一性，生成1,2-二氧戊环。相应的6-外向环化反应较慢，且立体选择性适中。在氢过氧化缩醛的情况下，醇盐的5-外向亲核转移与氢过氧化物的6-外向进攻有效竞争。
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