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 Incoordinate 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)isoborneol 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
Publication statusPublished - May 3 1995
Externally publishedYes

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Amino alcohols
Amino Alcohols
Aldehydes
Catalysis
Stereoselectivity
Catalysts
Stereoisomerism
Alkylation
Dimers
Alcohols
isoborneol

ASJC Scopus subject areas

  • Chemistry(all)

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Self and nonself recognition of asymmetric catalysts. Nonlinear effects in the amino alcohol-promoted enantioselective addition of dialkylzincs to aldehydes. / Kitamura, Masato; Suga, Seiji; Niwa, Makoto; Noyori, Ryoji.

In: Journal of the American Chemical Society, Vol. 117, No. 17, 03.05.1995, p. 4832-4842.

Research output: Contribution to journalArticle

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