Enantiodivergent Synthesis of Allenes by Point-to-Axial Chirality Transfer

Roly J. Armstrong, Meganathan Nandakumar, Rafael M.P. Dias, Adam Noble, Eddie L. Myers, Varinder K. Aggarwal*

*Corresponding author for this work

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

15 Citations (Scopus)
303 Downloads (Pure)

Abstract

An enantiodivergent method for the synthesis of multiply substituted allenes is described. Highly enantioenriched, point-chiral boronic esters were synthesized by homologation of α-seleno alkenyl boronic esters with lithiated carbamates and eliminated to form axially chiral allene products. By employing either oxidative or alkylative conditions, both syn and anti elimination could be achieved with complete stereospecificity. The process enables the synthesis of either M or P allenes from a single isomer of a point-chiral precursor and can be employed for the enantioselective assembly of di-, tri-, and tetrasubstituted allenes.

Original languageEnglish
Pages (from-to)8203-8208
Number of pages6
JournalAngewandte Chemie - International Edition
Volume57
Issue number27
Early online date30 May 2018
DOIs
Publication statusPublished - Jul 2018

Keywords

  • allenes
  • boronic esters
  • elimination
  • enantiodivergent reactions
  • enantiospecific reactions

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