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Synthesis 2014; 46(13): 1815-1822
DOI: 10.1055/s-0033-1341086
DOI: 10.1055/s-0033-1341086
paper
Regioselectivity in the Ring Opening of Epoxides: A Metal-Free Cascade C–S/C–O Bond Formation Approach to 1,3-Oxathiolan-2-ylidenes through Heteroannulation of α-Enolic Dithioesters at Room Temperature
Further Information
Publication History
Received: 23 January 2014
Accepted after revision: 10 March 2014
Publication Date:
17 April 2014 (online)
Abstract
An operationally simple and efficient approach to hitherto unreported and synthetically demanding 1,3-oxathiolan-2-ylidenes has been developed. The approach involves a cascade [2+3] heteroannulation of α-enolic dithioesters with epoxides promoted by non-nucleophilic moderate base Cs2CO3 at room temperature. Typical features of this strategy include metal-free mild reaction conditions, atom-economy, high yields, and efficacy of forming two consecutive C–S and C–O bonds, and one ring in a single stroke. MeSH is the only by-product, and the stereochemistry of the exocyclic α-oxoketene moiety of 1,3-oxathiolane was assigned to have Z-configuration.
Key words
epoxides - oxathiolanes - heteroannulation - metal-free conditions - regioselective - cascade reactionSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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