Cooperative catalysis of samarium diiodide and mercaptan in a stereoselective one-pot transformation of 5-oxopentanals into δ-lactones

JL Hsu, CT Chen, JM Fang

Index: Hsu, Jue-Liang; Chen, Chao-Tsen; Fang, Jim-Min Organic Letters, 1999 , vol. 1, # 12 p. 1989 - 1991

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Citation Number: 15

Abstract

We demonstrate a general method for conversion of various 5-oxopentanals to substituted δ- lactones and 1-oxa-2-decalones by the synergistic catalysis of samarium diiodide and 2- propanethiol (or disulfide). The deliberate use of mercaptan is advantageous to facilitate the catalytic cycle. This method shows high stereoselectivities, and an enantioselective procedure is feasible by using the chiral mercaptan (1 R, 2 S)-1-phenyl-2-(N-acetamido) ...