Asymmetric Traceless Petasis Borono-Mannich Reactions of Enals: Reductive Transposition of Allylic Diazenes

Yao Jiang, Regan J. Thomson*, Scott E. Schaus

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

The traceless Petasis borono-Mannich reaction of enals, sulfonylhydrazines, and allylboronates, catalyzed by chiral biphenols, results in an asymmetric reductive transposition of the in situ generated allylic diazene. Acyclic 1,4-diene products bearing either alkyl- or aryl-substituted benzylic stereocenters are afforded in excellent yields and enantiomeric ratios of up to 99:1. The use of crotylboronates in the reaction results in concomitant formation of two stereocenters in either a 1,4-syn or anti relationship from the corresponding E- or Z-crotylboronate used in the reaction. The use of β-monosubstituted enals in the asymmetric traceless Petasis borono-Mannich reaction of crotylboronates installs tertiary methyl-bearing stereocenters in good yields and high enantioselectivities.

Original languageEnglish (US)
Pages (from-to)16631-16635
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number52
DOIs
StatePublished - Dec 22 2017

Keywords

  • allylic compounds
  • asymmetric synthesis
  • hydrazones
  • organocatalysis
  • rearrangements

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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