In- or in(I)-employed diastereoselective Reformatsky-type reactions with ketones: 1H NMR investigations on the active species.
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]
Babu
Srinivasarao Arulananda
SA
Department of Molecular Chemistry and Handai Frontier Research Center, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan. baba@chem.eng.osaka-u.ac.jp
Yasuda
Makoto
M
Shibata
Ikuya
I
Baba
Akio
A