Borylated Cyclopropanes as Spring-Loaded Entities: Access to Vicinal Tertiary and Quaternary Carbon Stereocenters in Acyclic Systems

André U. Augustin, Sergio Di Silvio, Ilan Marek

Research output: Contribution to journalArticlepeer-review

Abstract

Herein, we present the formation of acyclic frameworks bearing two consecutive stereocenters of either tertiary or quaternary nature starting from easily accessible cyclopropenes. This holistic approach involves a regio- and diastereoselective hydro- or carboborylation of substituted cyclopropenyl esters. Formation of boronate complexes of the latter via the addition of nucleophiles and subsequent stereospecific 1,2-migration with carbon-carbon bond cleavage delivered the title compounds.

Original languageEnglish
Pages (from-to)16298-16302
Number of pages5
JournalJournal of the American Chemical Society
Volume144
Issue number36
DOIs
StatePublished - 14 Sep 2022

All Science Journal Classification (ASJC) codes

  • General Chemistry
  • Biochemistry
  • Catalysis
  • Colloid and Surface Chemistry

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