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

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.[1]

References

  1. Intramolecular, reductive cyclization of beta-ketoisothiocyanates promoted by using samarium diiodide. Cho, M.S., Lee, I.S., Kang, S.H., Kim, Y.H. Chemistry (Weinheim an der Bergstrasse, Germany) (2005) [Pubmed]
 
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