PtCl2-Catalyzed Cycloisomerization of 1,8-Enynes: Synthesis of Tetrahydropyridine Species

Anvar Mirzaei; Xiao-Shui Peng; Henry N C Wong

doi:10.1021/acs.orglett.9b01250

PtCl₂-Catalyzed Cycloisomerization of 1,8-Enynes: Synthesis of Tetrahydropyridine Species

Org Lett. 2019 May 17;21(10):3795-3798. doi: 10.1021/acs.orglett.9b01250. Epub 2019 May 1.

Authors

Anvar Mirzaei¹, Xiao-Shui Peng^{1

2}, Henry N C Wong^{1

2}

Affiliations

¹ Department of Chemistry, and State Key Laboratory of Synthetic Chemistry , The Chinese University of Hong Kong , Shatin , New Territories , Hong Kong SAR, China.
² Shenzhen Center of Novel Functional Molecules, Shenzhen Research Institute , The Chinese University of Hong Kong , No.10, Second Yuexing Road , Shenzhen 518507 , P.R. China.

PMID: 31042044
DOI: 10.1021/acs.orglett.9b01250

Abstract

The cycloisomerization of 1,8-enynes in the presence of platinum(II) chloride was developed to generate bicyclic nitrogen-containing heterocycle species via 6- endo-dig cyclization and [3,3]-sigmatropic rearrangement in acceptable to good yields. The related control experiments and preliminary mechanistic studies indicate a plausible mechanism involving 1,6- endo-dig aminoplatination of the alkyne and allylic [3,3]-sigmatropic rearrangement with total inversion of the allylic moiety.

Publication types

Research Support, Non-U.S. Gov't