Catalysis by amino acid-derived tetracoordinate complexes: Enantioselective addition of dialkylzincs to aliphatic and aromatic aldehydes

Brian D. Dangel, Robin L Polt

Research output: Contribution to journalArticle

56 Citations (Scopus)

Abstract

Me2Zn and Et2Zn added to aromatic and aliphatic aldehydes in the presence of 3 mol % of 2. (S)-1-Phenylethanol (91% ee) and (S)-1-phenylpropanol (86% ee) were synthesized from benzaldehyde and (S)-1-furan-2-yl-1-propanol (86% ee) from 2-furaldehyde. Nonanal and 3-phenylpropanal provided (S)-3-undecanol (96% ee) and (S)-1-phenyl-3-pentanol (94% ee). A solid-phase variant was effective with reduced ee's (e.g., 86% ee → 79% ee) for (S)-1-phenylpropanol.

Original languageEnglish (US)
Pages (from-to)3003-3006
Number of pages4
JournalOrganic Letters
Volume2
Issue number19
StatePublished - Sep 21 2000

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furans
Catalysis
aldehydes
Aldehydes
catalysis
amino acids
solid phases
Pentanols
Furaldehyde
Amino Acids
1-Propanol
1-phenylpropanol
benzaldehyde
furan
nonanal
3-phenylpropanal
methylphenyl carbinol

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Catalysis by amino acid-derived tetracoordinate complexes : Enantioselective addition of dialkylzincs to aliphatic and aromatic aldehydes. / Dangel, Brian D.; Polt, Robin L.

In: Organic Letters, Vol. 2, No. 19, 21.09.2000, p. 3003-3006.

Research output: Contribution to journalArticle

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