Oxa- and Azacycle-Formation via Migrative Cyclization of Sulfonylalkynol and Sulfonylalkynamide

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


This chapter described how NHC promotes cyclization of sulfonylalkynols and sulfonylalkynamides in an a4 Umpolung-type bond formation process that accompanied 1,2-migration of the sulfonyl groups. This reaction provides a novel access to oxa- and azacycles possessing a pendant vinyl sulfone functionality, which in turn is amenable to further transformations. During research on this migrative cyclization, mechanism studies indicated that nucleophiles other than NHCs might also induce this transformation. Further investigations showed that a catalytic amount of phosphine or 4-(N,N-dimethylamino)pyridine (DMAP) also promoted migrative cyclization in an a4 Umpolung manner similarly. Furthermore, asymmetric induction was observed when a chiral DMAP derivative was used in the reaction.


a4 Umpolung Sulfonylalkynol Sulfonylalkynamide Migrative cyclization Heterocycle formation 


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© Springer Nature Singapore Pte Ltd. 2019

Authors and Affiliations

  1. 1.Graduate School of Pharmaceutical SciencesKyoto UniversityKyotoJapan

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