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SmI2-promoted Reformatsky-type reaction and acylation of alkyl 1-chlorocyclopropanecarboxylates

SmI2-promoted Reformatsky-type reaction and acylation of alkyl 1-chlorocyclopropanecarboxylates

Organic Letters 10(23): 5453-5456

In the presence of HMPA in THF, highly stereoselective SmI(2)-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).

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Accession: 055815808

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PMID: 18989968

DOI: 10.1021/ol8022038

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