Nagano, Takao Motoyoshiya, Jiro Kakehi, Akikazu Nishii, Yoshinori SmI<sub>2</sub>-Promoted Reformatsky-Type Reaction and Acylation of Alkyl 1-Chlorocyclopropanecarboxylates In the presence of HMPA in THF, highly stereoselective SmI<sub>2</sub>-promoted substitutions of alkyl 1-chlorocyclopropanecarboxylates <b>1</b> using various ketones, aldehydes (Reformatsky-type reaction), and acyl chlorides (acylation) proceeded to give <i>trans</i>-adducts (<b>2</b> or <b>5</b>) in good to high yield with excellent <i>trans</i>-stereoselectivity (<i>trans</i>-add/<i>cis</i>-add = > 99/1). The Reformatsky-type reaction of <b>1</b> with aldehydes and unsymmetrical ketones proceeded with moderate diastereoselectivity (<i>re</i>-face-adduct/<i>si</i>-face-adduct = 60/40−75/25). presence;HMPA;stereoselective;diastereoselectivity;Acylation;acyl chlorides;Chlorocyclopropanecarboxylate;acylation;SmI;unsymmetrical ketones;chlorocyclopropanecarboxylate;aldehyde;Alkyl;substitution;THF;alkyl 2008-12-04
    https://acs.figshare.com/articles/journal_contribution/SmI_sub_2_sub_Promoted_Reformatsky_Type_Reaction_and_Acylation_of_Alkyl_1_Chlorocyclopropanecarboxylates/2895208
10.1021/ol8022038.s001