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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

Organic Letters 6(24): 4475-4478

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 9a(1)() and 13a(1)(), conclusively revealed the stereochemistry of the reaction path. (1)H NMR investigations revealed the formation of two types of alpha-metalated transient species from alpha-halo esters with In or In(I) halides. [reaction: see text]

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Accession: 049318611

Download citation: RISBibTeXText

PMID: 15548054

DOI: 10.1021/ol0482846

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