%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