Diastereoselective alkylations of chiral, phosphorus-stabilized carbanions: N-alkyl substituent effects in P-alkyl-1,3,2-diazaphosphorinane 2-oxides

S. E. Denmark, J. H. Kim

Research output: Contribution to journalArticlepeer-review

Abstract

A systematic study of the diastereoselective alkylation of anions derived from racemic N-substituted P-alkyl 1,3,2-diazaphosphorinane 2-oxides was carried out with variation of the N-substituent. High diastereoselectivity for the methylation of a P-benzyl anion has been achieved with N-neopentyl derivative 5d. Similarly, a P-ethyl anion derived from N-neopentyl derivative 6d showed high diastereoselectivity upon benzylation. The observed difference in alkylation diastereoselectivity between P-ethyl and P-benzyl anions for various N-alkyl substituents is discussed.

Original languageEnglish (US)
Pages (from-to)673-688
Number of pages16
JournalCanadian Journal of Chemistry
Volume78
Issue number6
DOIs
StatePublished - 2000

Keywords

  • Alkylation
  • Asymmetric
  • Organolitihium
  • Phosphonamide-stabilized carbanions
  • Stereoselective

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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