Self and Nonself Recognition of Asymmetric Catalysts. Nonlinear Effects in the Amino Alcohol-Promoted Enantioselective Addition of Dialkylzincs to Aldehydes

Masato Kitamura, Seiji Suga, Makoto Niwa, Ryoji Noyori

Research output: Contribution to journalArticle

218 Citations (Scopus)

Abstract

Chiral β-dialkylamino alcohols promote enantioselective alkylation of aldehydes by dialkylzincs, where a tricoordinate alkylzinc aminoalkoxide in equilibrium with its dimer acts as a true catalyst. The presence of other aminoalkoxides causes nonlinear effects on the rate and stereoselectivity of the enantioselective catalysis. This is a general phenomenon where the extent of the departure from the linearity is highly affected by the nature of the amino alcohols. Systematic investigation using (2S)-3-exo-(dimethylamino)isobomeol and its stereoisomers as well as achiral 2-(dimethylamino)-1,1-dimethylethanol has revealed that the self and nonself recognition of the asymmetric catalysts are the major source of this unusual phenomena. The relative significance of these recognitions affects the overall profile of asymmetric catalysis.

Original languageEnglish
Pages (from-to)4832-4842
Number of pages11
JournalJournal of the American Chemical Society
Volume117
Issue number17
DOIs
Publication statusPublished - May 1995
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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