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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
The thiopyran route to polypropionates.
1Department of Chemistry, University of Saskatchewan, Saskatoon, SK S7N 5C9, Canada. dale.ward@usask.ca
Chemical Communications (Cambridge, England)
|July 16, 2011
Summary
Thiopyran templates are versatile tools in organic synthesis, enabling complex polypropionate construction. This review highlights their strategic applications in stereoselective reactions and chemoenzymatic syntheses.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Stereoselective Synthesis
Background:
- The use of thiopyran templates in polypropionate synthesis was established in Woodward's 1981 erythromycin A total synthesis.
- Exploitation of fused bicyclic systems demonstrated the utility of thiopyran motifs.
Purpose of the Study:
- To review the strategic applications of thiopyran motifs in organic synthesis over three decades.
- To highlight their role in stereoselective transformations.
Main Methods:
- Review of literature on thiopyran template applications.
- Analysis of key stereoselective transformations facilitated by thiopyran motifs.
Main Results:
- Thiopyran motifs serve as unique substrates for chemoenzymatic syntheses.
- They act as surrogates for 3-pentanone in enantioselective aldol reactions.
- Thiopyran templates are effective for enantiotopic group selective reactions.
Conclusions:
- Thiopyran templates offer diverse strategic advantages in complex molecule synthesis.
- Their application has expanded significantly since their initial demonstration.
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