Preparation of Tethered Aldehyde Ynoates and Ynones by Ring Fragmentation of Cyclic γ-Oxy-β-hydroxy-α-diazo Carbonyls
Preparation of Tethered Aldehyde Ynoates and Ynones by Ring Fragmentation of Cyclic γ-Oxy-β-hydroxy-α-diazo Carbonyls
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DOI：
10.1021/jo902405f
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发表时间：
2010-01-15
影响因子：
3.6
通讯作者：
Brewer, Matthias
中科院分区：
文献类型：
--
作者：
Bayir, Ali;Draghici, Cristian;Brewer, Matthias
环状γ-氧-β-羟基-α-重氮羰基化合物经历刘易斯酸诱导的环断裂，以提供与醛、酮或酯连接的炔酸酯或炔酮。通过将锂化的α-重氮羰基化合物加入到α-氧基酮中，可以方便地制备断裂前体。片段化表现出一般性，并以良好至优异的产率提供多种富含官能团的产物。
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.