Catalytic enantioselective [2,3]-rearrangements of amine N-oxides

Hongli Bao, Xiangbing Qi, Uttam K. Tambar

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

The first Pd-catalyzed enantioselective [2,3]-rearrangement of allylic amine N-oxides is described, which formally represents an asymmetric Meisenheimer rearrangement. The mild reaction conditions enable the synthesis of chiral nonracemic aliphatic allylic alcohol derivatives with reactive functional groups. On the basis of preliminary studies, a cyclization-mediated mechanism is proposed.

Original languageEnglish (US)
Pages (from-to)1206-1208
Number of pages3
JournalJournal of the American Chemical Society
Volume133
Issue number5
DOIs
StatePublished - Feb 9 2011

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Cyclization
Oxides
Functional groups
Amines
Alcohols
Derivatives
allyl alcohol

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Catalytic enantioselective [2,3]-rearrangements of amine N-oxides. / Bao, Hongli; Qi, Xiangbing; Tambar, Uttam K.

In: Journal of the American Chemical Society, Vol. 133, No. 5, 09.02.2011, p. 1206-1208.

Research output: Contribution to journalArticle

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