Diiodomethane-Samarium iodide

Samarium Compounds t-Butoxydiiodosamarium, 272 Diiodomethane-Samarium, 113 Diiodomethane-Samarium iodide, 113 Samarium, 113... 

Reduction of A,(V-di bcnzy lam i noalkyl chloromethyl ketones 133, followed by spontaneous intramolecular ring closure of the resulting 7-chloroamines 134, afforded azetidinium salts 135, which were subsequently deprotected toward chiral 3-hydroxyazetidines 136 and 137 (Scheme 29) <1997JOC1815>. In a similar approach, ct-amino aldehydes 138 were converted into 3-hydroxyazetidinium salts 139 upon treatment with diiodomethane and samarium iodide, followed by stabilization using AgBF4. Ar-Dealkylation with Pd afforded enantiopure azetidines 140 (Scheme 30) <2000TL1231>. 

Samarium(II) iodide and diiodomethane efficiently cyclopropanated lithium enolates 119 under very mild conditions, providing a convenient route to cyclopropanols 120. 

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