Regioselective anti-Silyllithiation of Propargylic Amines

Abstract

The regioselective anti-silyllithiation of propargylic amines is developed to facilitate the efficient synthesis of alkenylsilanes. This reaction generates an alkenyllithium intermediate that is stabilized by the formation of a five-membered cyclic structure through intramolecular coordination of the nitrogen functional group. Upon subsequent treatment with an electrophile, the alkenyllithium intermediate is further functionalized to afford tetrasubstituted allylic amines bearing a β-silicon substituent.

Key words

silyllithium - alkenylsilane - allylamine - one-pot synthesis - remote stereocontrol

Publikationsverlauf

Eingereicht: 06. Februar 2023

Angenommen nach Revision: 06. März 2023

Accepted Manuscript online:
06. März 2023

Artikel online veröffentlicht:
12. April 2023

• References and Notes

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