Allenoate Prenucleophiles: A Triply Diastereoselective Approach to β-Hydroxy Esters Containing All-Carbon α-Quaternary Centers.
Allenoate Prenucleophiles: A Triply Diastereoselective Approach to β-Hydroxy Esters Containing All-Carbon α-Quaternary Centers.
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联烯酸亲核体：含有全碳α-四元中心的β-羟基酯的三重非对映选择性方法。
DOI：
10.1021/acs.orglett.9b02930
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发表时间：
2019
期刊：
影响因子：
5.2
通讯作者：
Lepore,SalvatoreD
中科院分区：
文献类型：
--
作者：
Maki,SamanthaL;Maity,Pradip;Dougherty,Shannon;Johns,Jennifer;Lepore,SalvatoreD
用钛（IV）活化的丙二烯基酯以高区域选择性和非对映选择性与各种醛加成，得到了具有α-乙烯基的全碳四元中心的产物，该中心具有高的Z-构型选择性。羟醛产物也转化为茚酮，为这一重要化合物类别提供了新的途径。产品三重非对映选择性已合理化使用协调过渡态模型。
Allenyl esters activated by titanium(IV) underwent additions to a wide range of aldehydes in high regio- and diastereoselectivities leading to products containing an all-carbon quaternary center bearing an α-vinyl group that was installed with high selectivity for theZ-geometry. An aldol product was also converted to an indanone offering a new route to this important compound class. Product triple diastereoselectivity has been rationalized using a concerted transition-state model.