Addition Reaction of Vinylic Reagents, Derived from  α ‐Chloroenones, to Carbonyl Compounds Promoted by Samarium Diiodide | Zendy

Concellón José M. | Zendy; Bernad Pablo L. | Zendy; Huerta Mónica | Zendy; GarcíaGranda Santiago | Zendy; Díaz M. Rosario | Zendy

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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.

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