Intramolecular, reductive cyclization of beta-ketoisothiocyanates promoted by using samarium diiodide

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A novel samarium diiodide (SmI2) promoted intramolecular cyclization of beta-ketoisothiocyanate, derived from alpha,beta-unsaturated esters and ammonium thiocyanate led to alpha-hydroxythiolactams and/or thiolactams in high yields. Treatment of beta-ketoisothiocyanate with two equivalents of SmI2 gave a mixture of alpha-hydroxythiolactam and thiolactam. Four equivalents of SmI2 afforded only thiolactam in high yields. The intramolecular cyclization took place with high to complete stereoselectivity. A mechanism to explain this transformation is proposed.
Publisher
WILEY-V C H VERLAG GMBH
Issue Date
2005-02
Language
English
Article Type
Article
Keywords

ORGANIC-SYNTHESIS; COUPLING REACTIONS; CARBONYL-COMPOUNDS; ORGANOPHOSPHORUS COMPOUNDS; IODIDE; SMI2; THIOLACTAMS; LANTHANIDES; CONVERSION; ESTERS

Citation

CHEMISTRY-A EUROPEAN JOURNAL, v.11, no.5, pp.1452 - 1458

ISSN
0947-6539
DOI
10.1002/chem.200400676
URI
http://hdl.handle.net/10203/89786
Appears in Collection
CH-Journal Papers(저널논문)
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