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Conclusion

  • Yinli WangEmail author
Chapter
Part of the Springer Theses book series (Springer Theses)

Abstract

In this thesis, the author developed a new oxa- and azacycle forming reaction using sulfonylalkynol and sulfonylalkynamide in the presence of a substoichiometric amount of NHC. This reaction proceeded in a4-Umpolung-type bond formation process that accompanied 1,2-migration of the sulfonyl groups. Investigation of the reaction mechanism showed that other nucleopiles may also promote this reaction instead of NHC. Actually, the triphenylphosphine was fount to give similar results with NHC. The possibility of enantiocontrol of this reaction was indicated by the use of chiral phosphine and binaphthyl-based chiral DMAP. Further investigation on developing an efficient enantioselective variant is currently in progress in this laboratory.

In this thesis, the author developed a new oxa- and azacycle forming reaction using sulfonylalkynol and sulfonylalkynamide in the presence of a substoichiometric amount of NHC. This reaction proceeded in a4-Umpolung-type bond formation process that accompanied 1,2-migration of the sulfonyl groups. Investigation of the reaction mechanism showed that other nucleopiles may also promote this reaction instead of NHC. Actually, the triphenylphosphine was fount to give similar results with NHC. The possibility of enantiocontrol of this reaction was indicated by the use of chiral phosphine and binaphthyl-based chiral DMAP. Further investigation on developing an efficient enantioselective variant is currently in progress in this laboratory.

In addition, the author developed the first kinetic resolution of α-hydroxy thioamide using a new aminoindane-based triazolium salt and low acidic carboxylic acid cocatalyst. The in situ generated catboxylate was found to associate with α-hydroxy thioamide through hydrogen bond formation, which was recognized by chiral NHC during the acylation process.

Copyright information

© Springer Nature Singapore Pte Ltd. 2019

Authors and Affiliations

  1. 1.Graduate School of Pharmaceutical SciencesKyoto UniversityKyotoJapan

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