The catalytic asymmetric diels-alder reactions and post-cycloaddition reductive transpositions of 1-hydrazinodienes

Hao Xie, Glenn M. Sammis, Eric M. Flamme, Christina M. Kraml, Erik J. Sorensen

Research output: Contribution to journalArticle

9 Scopus citations

Abstract

Cycling through: Type I cyclohexenes are produced with high margins of stereoselectivity by chiral, catalyst-controlled, Diels-Alder reactions between 1-hydrazinodienes and N-acryloyl oxazolidinone dienophiles, and readily transformed to cyclohexenes III via a putative, transient allylic diazene II (see scheme). This chemistry gives access to functionalized cyclohexenes that can be difficult to construct by alternative methods.

Original languageEnglish (US)
Pages (from-to)11131-11134
Number of pages4
JournalChemistry - A European Journal
Volume17
Issue number40
DOIs
StatePublished - Sep 26 2011

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Keywords

  • asymmetric Diels-Alder reaction
  • cyclization
  • cycloaddition
  • hydrazinodienes
  • sigmatropic rearrangement

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