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Addition Reaction of Vinylic Reagents, Derived from α ‐Chloroenones, to Carbonyl Compounds Promoted by Samarium Diiodide
Author(s) -
Concellón José M.,
Bernad Pablo L.,
Huerta Mónica,
GarcíaGranda Santiago,
Díaz M. Rosario
Publication year - 2003
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200304954
Subject(s) - samarium , reagent , acetonitrile , chemistry , diastereomer , samarium diiodide , ketone , medicinal chemistry , double bond , yield (engineering) , reaction mechanism , organic chemistry , catalysis , materials science , metallurgy
A new samarium diiodide‐promoted addition reaction of vinylsamarium reagents, derived from ( Z )‐ α ‐chloro‐ α , β ‐unsaturated phenones 1 , to both ketones (in THF) and aldehydes (in acetonitrile) led to ( Z )‐2‐(1‐hydroxyalkyl)‐2,3‐unsaturated ketones in good yield. These transformations took place with total or very high inversion of the stereochemistry of the CC double bond of the starting chloroenone, producing the Z diastereoisomer. A new methodology to prepare SmI 2 in acetonitrile by sonic treatment of 1,2‐diiodoethane with Sm powder is also described. A mechanism to explain this transformation is proposed.