Enantioselective construction of quaternary α-carbon centers on α-amino phosphonates via catalytic asymmetric allylation

Ryoichi Kuwano, Ryo Nishio, Yoshihiko Ito

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Abstract

(equation presented) Asymmetric allylation of α-acetamido β-keto phosphonates was promoted, in the presence of potassium tert-butoxide as a base, by a palladium catalyst prepared from [Pd(π-allyl)(cod)]BF4 and (R)-BINAP and gave the corresponding α-alkyl α-amino phosphonic acid derivatives with 65-88% ee. Diastereoselective reduction of the carbonyl group in the product was accomplished by NaBH4 or Bu4NBH4. The diastereoselection in the reduction was reversed by choice of solvent.

Original languageEnglish
Pages (from-to)837-839
Number of pages3
JournalOrganic letters
Volume1
Issue number6
DOIs
Publication statusPublished - Sep 23 1999

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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