Synthesis of allenylzinc reagents by 1,2-rearrangement of alkynyl(disilyl)zincates derived from acetylenic epoxides andacetylenic aziridines

Valentin Bochatay, Laurent Debien, Fabrice Chemla, Franck Ferreira, Olivier Jackowski, Alejandro Perez-Luna

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Abstract

Lithium alkynyl(disilyl)zincates obtained from metalated ethynyloxiranes, as well as from N-tert-butanesulfinyl(ethynyl)aziridines or N-tert-butanesulfonyl(ethynyl)aziridines, undergo 1,2-migration of the organosilyl group with ring opening of the oxirane or aziridine ring by S Ni displacement. A developed protocol that involves nBuLi for the metalation step offers a straightforward approach to the corresponding δ-oxy- and δ-amino α-silyl allenylzinc intermediates. The reagents derived from the epoxides are amenable to subsequent in situ condensation with aldehydes or ketones to provide 1,3-diols but not those derived from aziridines that only react sluggishly in similar condensations.

Original languageEnglish
Pages (from-to)609-616
Number of pages8
JournalComptes Rendus Chimie
Volume20
Issue number6
DOIs
Publication statusPublished - 1 Jun 2017
Externally publishedYes

Keywords

  • Alkynes
  • Carbenoids
  • Rearrangement
  • Silicon
  • Zinc

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