Preparation of Tethered Aldehyde Ynoates and Ynones by Ring Fragmentation of Cyclic γ-Oxy-β-hydroxy-α-diazo Carbonyls

被引：28

作者：

Bayir, Ali ^{[1
]}

Draghici, Cristian ^{[1
]}

Brewer, Matthias ^{[1
]}

机构：

[1] Univ Vermont, Dept Chem, 82 Univ Pl, Burlington, VT 05405 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 02期

基金：

美国国家科学基金会;

关键词：

HETEROLYTIC FRAGMENTATION; ACETYLENIC KETONES; ORGANIC-SYNTHESIS; BOND-CLEAVAGE; AMINO-ACIDS; FRAGMENTIERUNG; REARRANGEMENTS; CYCLOADDITION; GENERATION; ALLENES;

D O I：

10.1021/jo902405f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclic gamma-oxy-beta-hydroxy-alpha-diazo carbonyls undergo Lewis acid induced ring fragmentation to provide either ynoates or ynones tethered to an aldehyde, ketone, or ester. The fragmentation precursors are convenient to prepare by adding lithiated alpha-diazo carbonyls to alpha-oxy ketones. The fragmentation appears general and provides a variety of functional group-rich products in good to excellent yield.

引用

页码：296 / 302

页数：7

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