Synthesis of phosphoramides for the lewis base-catalyzed allylation and aldol addition reactions

Scott E. Denmark, Xiping Su, Yutaka Nishigaichi, Diane M. Coe, Ken Tsung Wong, Stephen B.D. Winter, Jun Young Choi

Research output: Contribution to journalArticle

Abstract

Both chiral and achiral phosphoramides of diverse structure were prepared from diamines by the coupling to phosphorus(V) or phosphorus(III) reagents. Several enantiopure 1,2-diphenyl-1,2-ethanediamine analogues have been prepared by the reductive coupling of the corresponding N-silylimine with NbCl4(THF)2 and subsequent resolution by the formation of diastereomeric menthyl carbamates. (S,S)-N,N'-Di-(1-naphthyl)-1,2-diphenyl- 1,2-ethanediamine 15 was prepared by the arylation of (S,S)-1,2-diphenyl- 1,2-ethanediamine with naphthyl iodide.

Original languageEnglish (US)
Pages (from-to)1958-1967
Number of pages10
JournalJournal of Organic Chemistry
Volume64
Issue number6
DOIs
StatePublished - Mar 19 1999

ASJC Scopus subject areas

  • Organic Chemistry

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    Denmark, S. E., Su, X., Nishigaichi, Y., Coe, D. M., Wong, K. T., Winter, S. B. D., & Choi, J. Y. (1999). Synthesis of phosphoramides for the lewis base-catalyzed allylation and aldol addition reactions. Journal of Organic Chemistry, 64(6), 1958-1967. https://doi.org/10.1021/jo9820723