Cooperative Catalysis of Samarium Diiodide and Mercaptan in a Stereoselective One-Pot Transformation of 5-Oxopentanals into £_-Lactones
Resource
Organic Letters 1 (12): 1989-1991
Journal
Organic Letters
Journal Volume
1
Journal Issue
12
Pages
1989-1991
Date Issued
1999
Date
1999
Author(s)
Abstract
(Matrix Presented) 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 (1R,2S)-1-phenyl-2-(N-acetamido)propanethiol as a promoter.
Type
journal article
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