Enantiospecific Alkynylation of Alkylboronic Esters

Yahui Wang, Adam Noble, Eddie L Myers, Varinder K Aggarwal

Research output: Contribution to journalArticle (Academic Journal)peer-review

36 Citations (Scopus)
344 Downloads (Pure)

Abstract

Enantioenriched secondary and tertiary alkyl pinacolboronic esters undergo enantiospecific deborylative alkynylation through a Zweifel-type alkenylation followed by a 1,2-elimination reaction. The process involves the use of α-lithio vinyl bromide or vinyl carbamate, species whose application to Zweifel-type reactions has not previously been explored. The resulting functionalized 1,1-disubstituted alkenes undergo facile base-mediated elimination to generate the terminal alkyne products in high yield and excellent levels of enantiospecificity over a wide range of pinacolboronic ester substrates. Furthermore, we have demonstrated that, in addition to terminal alkynes, internal and silyl-protected alkynes can be formed by simply introducing a suitable carbon- or silicon-based electrophile after the base-mediated 1,2-elimination reaction
Original languageEnglish
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number13
Early online date2 Mar 2016
DOIs
Publication statusPublished - 18 Mar 2016

Keywords

  • alkynes
  • boronic esters
  • alkynylation
  • synthetic methods

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