Alkene Dioxygenation with Malonoyl Peroxides: Synthesis of γ-Lactones, Isobenzofuranones, and Tetrahydrofurans

被引：38
|
作者：
Alamillo-Ferrer, Carla [1 ]
Karaboumiotis-Sotti, Marianna [1 ]
Kennedy, Alan R. [1 ]
Campbell, Matthew [2 ]
Tomkinson, Nicholas C. O. [1 ]
机构：
[1] Univ Strathclyde, Dept Pure & Appl Chem, WestCHEM, 295 Cathedral St, Glasgow G1 1XL, Lanark, Scotland
[2] GlaxoSmithKline Med Res Ctr, Gunnels Wood Rd, Stevenage SG1 2NY, Herts, England
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 13期
基金：
英国工程与自然科学研究理事会;
关键词：
FLUORINATED ALCOHOLS; SYN-DIHYDROXYLATION; RULES;
D O I：
10.1021/acs.orglett.6b01253
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Treatment of homoallylic alcohols or carboxylic acids with malonoyl peroxide 1 provides a stereoselective method for the preparation of tetrahydrofurans, gamma-lactones, and isobenzofuranones in 44-82% yield and up to 27:1 trans selectivity. Application of this simple and effective heterocyclization in the synthesis of the antidepressant citalopram is also described.
引用
收藏
页码：3102 / 3105
页数：4
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