%0 Journal Article
%A Nagano, Takao
%A Motoyoshiya, Jiro
%A Kakehi, Akikazu
%A Nishii, Yoshinori
%D 2008
%T SmI2-Promoted Reformatsky-Type Reaction and Acylation of Alkyl 1-Chlorocyclopropanecarboxylates
%U https://acs.figshare.com/articles/journal_contribution/SmI_sub_2_sub_Promoted_Reformatsky_Type_Reaction_and_Acylation_of_Alkyl_1_Chlorocyclopropanecarboxylates/2895208
%R 10.1021/ol8022038.s001
%2 https://acs.figshare.com/ndownloader/files/4593349
%K presence
%K HMPA
%K stereoselective
%K diastereoselectivity
%K Acylation
%K acyl chlorides
%K Chlorocyclopropanecarboxylate
%K acylation
%K SmI
%K unsymmetrical ketones
%K chlorocyclopropanecarboxylate
%K aldehyde
%K Alkyl
%K substitution
%K THF
%K alkyl
%X In the presence of HMPA in THF, highly stereoselective SmI2-promoted substitutions of alkyl 1-chlorocyclopropanecarboxylates 1 using various ketones, aldehydes (Reformatsky-type reaction), and acyl chlorides (acylation) proceeded to give trans-adducts (2 or 5) in good to high yield with excellent trans-stereoselectivity (trans-add/cis-add = > 99/1). The Reformatsky-type reaction of 1 with aldehydes and unsymmetrical ketones proceeded with moderate diastereoselectivity (re-face-adduct/si-face-adduct = 60/40−75/25).
%I ACS Publications