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Intramolecular,Reductive Cyclization of beta-Ketoisothiocyanates Promoted by Using Samarium Diiodide

机译:二碘化Sa促进β-酮异硫氰酸酯的分子内还原环化

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摘要

A novel samarium diiodide (SmI_2) promoted intramolecular cyclization of beta-ketoisothiocyanate,derived from alpha,beta-unsaturated esters and ammonium thio-cyanate led to alpha-hydroxythiolactams and/or thiolactams in high yields.Treatment of beta-ketoisothiocyanate with two equivalents of SmI_2 gave a mixture of a-hydroxy-thiolactam and thiolactam.Four equivalents of SmI_2 afforded only thiolactam in high yields.The intramolecular cyclization took place with high to complete ster-eoselectivity.A mechanism to explain this transformation is proposed.
机译:一种新型的二碘化((SmI_2)促进了α-β-不饱和酯和硫氰酸铵衍生的β-酮异硫氰酸酯的分子内环化反应,从而高产率地产生了α-羟基硫代内酰胺和/或硫代内酰胺。 SmI_2生成α-羟基-硫代内酰胺和硫代内酰胺的混合物。四当量的SmI_2仅以高收率提供硫代内酰胺。分子内环化反应具有很高的立体位选择性,提出了解释这种转化的机理。

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