Enantioselective addition of diethylzinc to aldehydes using 1,1′-bi-2-naphthol-3,3′-dicarboxamide as a chiral auxiliary

Chemistry Letters

Volumn , Issue 5, 1996, Pages 343-344

  Kitajima, Hiroshi ^a   Ito, Katsuji ^a   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030522386     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.343     Document Type: Article

References (15)

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5. For example, the addition of diethylzinc to phenylpropargylaldehyde in the presence of (S)-(+)-diphenyl(N-methylpyrrolidin-2-yl)methanol shows moderate 70% ee (reference 4), while chiral titanium catalysts shows high enantioselectivity (reference 5). The addition of diethylzinc to o-fuluorobenzaldehyde in the presence of titanium-TADDOLate catalyst also shows moderate 62% ee (reference 5a). However, reactions of other substrates using these chiral auxiliary or catalyst show excellent enantioselectivity.
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13. 1H NMR of 3 in THF-dg suggested that the complex existed as an equilibrium mixture of three species; monomer, dimer, and trimer.
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