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Synthesis 2016; 48(23): 4091-4098
DOI: 10.1055/s-0035-1562473
DOI: 10.1055/s-0035-1562473
paper
Diastereoselective Synthesis of Spiro[pyrazolone-4,3′-tetrahydrothiophenes] via a Sulfa-Michael/Aldol Domino Reaction
Further Information
Publication History
Received: 14 June 2016
Accepted: 14 June 2016
Publication Date:
12 August 2016 (online)
![](https://www.thieme-connect.de/media/synthesis/201623/lookinside/thumbnails/ss-2016-z0427-op_10-1055_s-0035-1562473-1.jpg)
Abstract
A new approach for the diastereoselective synthesis of spiro[pyrazolone-4,3′-tetrahydrothiophenes] was developed. The N,N-diisopropylethylamine-catalyzed reaction of arylidenepyrazolones with in situ generated 2-sulfanylacetaldehyde provides the corresponding spiro-heterocycles via a domino sulfa-Michael/aldol reaction in 42–98% yield and 3:2:1 to 20:1 d.r. under mild reaction conditions.
Key words
spiro compounds - domino reaction - tetrahydrothiophene - pyrazolone - sulfa-Michael additionSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562473.
- Supporting Information
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