Asymmetric catalysis with chiral Lewis bases

Scott E. Denmark, Robert A. Stavenger, Xiping Su, Ken Tsung Wong, Yutaka Nishigaichi

Research output: Contribution to journalArticle

Abstract

The trichlorosilyl enolates of methyl ketones, ethyl ketones and cycloalkanones react readily with a variety of aldehydes in aldol addition reactions without external promoters at 0°C - rt. The aldol products are generated in excellent yield and with good to excellent diastereoselectivity (E to syn, Z to anti). In the presence of catalytic amounts (5-15 mol %) of chiral phosphoramide promoters the aldol reactions of enoxytrichlorosilanes now proceed rapidly at -78°C and are extremely diastereoselective (E to anti, Z to syn, 61-99/1). The products are afforded with good to excellent enantioselectivity (anti: 82-97% ee, syn: 58-96% ee).

Original languageEnglish (US)
Pages (from-to)1469-1476
Number of pages8
JournalPure and Applied Chemistry
Volume70
Issue number8
DOIs
StatePublished - Aug 1998

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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    Denmark, S. E., Stavenger, R. A., Su, X., Wong, K. T., & Nishigaichi, Y. (1998). Asymmetric catalysis with chiral Lewis bases. Pure and Applied Chemistry, 70(8), 1469-1476. https://doi.org/10.1351/pac199870081469