The Application of 1,2-Silyl Shift in Synthesis of Pyrrolidine Derivatives from Propargylsilanes

12th Paul Walden Symposium on Organic Chemistry: Program and Abstract Book 2021
Rasma Kroņkalne, Māris Turks

In this work a new approach towards the synthesis of 2-(1-tertbutyldimethylsilyl) vinylpyrrolidines was investigated. By combining Staudinger reduction and subsequent acylation under various conditions, a two-step one-pot process for the synthesis of protected amines from (6-azidohex-1-yn-3-yl)(tert-butyl)dimethylsilane was designed. Cyclization of propargylsilanes was achieved through electrophilic activation of the alkyne, followed by intramolecular nucleophile attack on the formed carbocation, yielding pyrrolidines.

Keywords
1,2-SILYL SHIFT, PROPARGYL SILANES, PYRROLIDINES
Hyperlink
https://walden.osi.lv/wp-content/uploads/2021/10/12th_P.Walden_Symposium_Program.Abstract_BOOK.pdf

Kroņkalne, R., Turks, M. The Application of 1,2-Silyl Shift in Synthesis of Pyrrolidine Derivatives from Propargylsilanes. In: 12th Paul Walden Symposium on Organic Chemistry: Program and Abstract Book, Latvia, Riga, 28-29 October, 2021. Riga: 2021, pp.44-44.

Publication language
English (en)