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

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Lewis Bases
Ketones
Catalysis
Addition reactions
Enantioselectivity
Aldehydes
3-hydroxybutanal

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

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

Asymmetric catalysis with chiral Lewis bases. / Denmark, Scott E.; Stavenger, Robert A.; Su, Xiping; Wong, Ken Tsung; Nishigaichi, Yutaka.

In: Pure and Applied Chemistry, Vol. 70, No. 8, 08.1998, p. 1469-1476.

Research output: Contribution to journalArticle

Denmark, SE, Stavenger, RA, Su, X, Wong, KT & Nishigaichi, Y 1998, 'Asymmetric catalysis with chiral Lewis bases', Pure and Applied Chemistry, vol. 70, no. 8, pp. 1469-1476. https://doi.org/10.1351/pac199870081469
Denmark, Scott E. ; Stavenger, Robert A. ; Su, Xiping ; Wong, Ken Tsung ; Nishigaichi, Yutaka. / Asymmetric catalysis with chiral Lewis bases. In: Pure and Applied Chemistry. 1998 ; Vol. 70, No. 8. pp. 1469-1476.
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