Catalytic asymmetric claisen rearrangement of enolphosphonates: Construction of vicinal tertiary and all-carbon quaternary centers

Jiajing Tan, Cheol-Hong Cheon, Hisashi Yamamoto

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

A copper-catalyzed enantioselective Claisen rearrangement of easily accessible enolphosphonates using the commercially available PhBOX as the chiral ligand was developed. A wide range of rearrangement products with contiguous tertiary and all-carbon quaternary centers were obtained in excellent yields and stereoselectivities. The α-ketophosphonate substituent in the products could be easily transformed into other functional groups.

Original languageEnglish
Pages (from-to)8264-8267
Number of pages4
JournalAngewandte Chemie - International Edition
Volume51
Issue number33
DOIs
Publication statusPublished - 2012 Aug 13

Fingerprint

Stereoselectivity
Functional groups
Copper
Carbon
Ligands

Keywords

  • asymmetric catalysis
  • BOX ligands
  • Claisen rearrangement
  • copper
  • quaternary carbon centers

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

Catalytic asymmetric claisen rearrangement of enolphosphonates : Construction of vicinal tertiary and all-carbon quaternary centers. / Tan, Jiajing; Cheon, Cheol-Hong; Yamamoto, Hisashi.

In: Angewandte Chemie - International Edition, Vol. 51, No. 33, 13.08.2012, p. 8264-8267.

Research output: Contribution to journalArticle

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