Synthesis of functionalized chiral (racemic) cyclobutanones

被引：18

作者：

Riches, AG ^{[1
]}

Wernersbach, LA ^{[1
]}

Hegedus, LS ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 14期

关键词：

D O I：

10.1021/jo980282+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral (racemic) cyclobutanones, produced by the photochemical reaction between chiral ene carbamates and chromium alkoxycarbene complexes, were functionalized in several ways. Enolization/O-alkylation produced enol ethers and esters that underwent facile ring opening to produce electron-rich dienes. Epoxidation of the silyl enol ether followed by epoxide opening produced alpha-(silyloxy)cyclobutanones. alpha-Bromination (NBS) of the cyclobutanones followed by Baeyer-Villiger oxidation led to alpha-bromobutyrolactones that could be converted to butenolides. By using alpha-stannyl ene carbamates as substrates for the photochemical cycloaddition, beta-stannyl cyclobutanones were produced.

引用

页码：4691 / 4696

页数：6

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