用H₂O₂和烷基氢过氧化物开环取代的氧杂环丁烷：立体选择性合成3-过氧醇和1,2,4-三氧杂环庚烷的方法。

Opening of substituted oxetanes with H(2)O(2) and alkyl hydroperoxides: stereoselective approach to 3-peroxyalcohols and 1,2,4-trioxepanes.

作者信息

Dussault Patrick H, Trullinger Tony K, Noor-e-Ain Farhana

机构信息

Department of Chemistry, University of Nebraska-Lincoln, Lincoln, Nebraska 68588-0304, USA.

出版信息

Org Lett. 2002 Dec 26;4(26):4591-3. doi: 10.1021/ol0265259.

DOI:10.1021/ol0265259

PMID:12489937

Abstract

[reaction: see text] Lewis acid-catalyzed opening of oxetanes by hydrogen peroxide proceeds regioselectively and with good to moderate stereoselectivity to furnish enantiomerically enriched 3-hydroperoxyalkanols. The corresponding opening using alkyl hydroperoxides furnishes 3-peroxyalkanols. The hydroperoxyalkanols are easily converted into enantiomerically enriched 1,2,4-trioxepanes, building blocks for antimalarials.

摘要

[反应：见正文] 路易斯酸催化下，过氧化氢使氧杂环丁烷开环反应具有区域选择性，且立体选择性良好至中等，可得到对映体富集的3-氢过氧链烷醇。使用烷基氢过氧化物进行相应的开环反应可得到3-过氧链烷醇。氢过氧链烷醇可轻松转化为对映体富集的1,2,4-三氧杂环庚烷，这是抗疟药物的结构单元。