In- or In(I)-employed diastereoselective Reformatsky-type reactions with ketones:: 1H NMR investigations on the active species
In- or In(I)-employed diastereoselective Reformatsky-type reactions with ketones:: 1H NMR investigations on the active species
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DOI：
10.1021/ol0482846
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发表时间：
2004-11-25
期刊：
影响因子：
5.2
通讯作者：
Baba, A
中科院分区：
文献类型：
--
作者：
Babu, SA;Yasuda, M;Baba, A
报道了一种基于In或In（I）的高效立体选择性C-C键形成反应：酮的非对映选择性Reformatsky型反应。通过对相应的醇gal和13（a1）的酯衍生物的X射线结构分析证实了主要的反式异构体的形成，最终揭示了反应路径的立体化学。H-1 NMR研究揭示了从α-卤代酯与In或In（I）卤化物形成两种类型的α-金属化过渡物种。
An efficient In- or In(I)-based stereoselective C-C bond formation is reported; the diastereoselective Reformatsky-type reactions of ketones. The predominant formations of anti isomers, confirmed by the X-ray structure analyses of ester derivatives of respective alcohols gal and 13(a1), conclusively revealed the stereochemistry of the reaction path. H-1 NMR investigations revealed the formation of two types of alpha-metalated transient species from a-halo esters with In or In(I) halides.