Design of chiral catalysis and asymmetric autocatalysis for the enantioselective additions of organozinc reagents

Kenso Soai, Takanori Shibata

Research output: Contribution to journalArticle

41 Citations (Scopus)

Abstract

Diphenyl(1-methylpyrrolidin-2-yl)methanol (DPMPM) and N,N-dibutylnorephedrine (DBNE) are highly enantio- and chemoselective chiral catalysts for the addition of dialkylzincs to various aldehydes, affording sec-alcohols with high enantiomeric excesses. Heterogeneous chiral catalyst supported on polystyrene is also highly enantioselective. Pyrimidyl and quinolyl alkanols are asymmetric autocatalysts with amplification of enantiomeric excess in the enantioselective isopropylation of aldehydes. Enantioselective addition of dialkylzincs to N-diphenylphosphinylimines and conjugate addition to enones are performed using N,N-dialkylnorephedrines.

Original languageEnglish
Pages (from-to)994-1005
Number of pages12
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume55
Issue number11
Publication statusPublished - 1997 Nov
Externally publishedYes

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Aldehydes
Catalysis
Polystyrenes
Catalyst supports
Amplification
Methanol
Alcohols
Catalysts
diphenyl

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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abstract = "Diphenyl(1-methylpyrrolidin-2-yl)methanol (DPMPM) and N,N-dibutylnorephedrine (DBNE) are highly enantio- and chemoselective chiral catalysts for the addition of dialkylzincs to various aldehydes, affording sec-alcohols with high enantiomeric excesses. Heterogeneous chiral catalyst supported on polystyrene is also highly enantioselective. Pyrimidyl and quinolyl alkanols are asymmetric autocatalysts with amplification of enantiomeric excess in the enantioselective isopropylation of aldehydes. Enantioselective addition of dialkylzincs to N-diphenylphosphinylimines and conjugate addition to enones are performed using N,N-dialkylnorephedrines.",
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AB - Diphenyl(1-methylpyrrolidin-2-yl)methanol (DPMPM) and N,N-dibutylnorephedrine (DBNE) are highly enantio- and chemoselective chiral catalysts for the addition of dialkylzincs to various aldehydes, affording sec-alcohols with high enantiomeric excesses. Heterogeneous chiral catalyst supported on polystyrene is also highly enantioselective. Pyrimidyl and quinolyl alkanols are asymmetric autocatalysts with amplification of enantiomeric excess in the enantioselective isopropylation of aldehydes. Enantioselective addition of dialkylzincs to N-diphenylphosphinylimines and conjugate addition to enones are performed using N,N-dialkylnorephedrines.

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