Enantioselective addition of diethylzinc to aldehydes using 2-azanorbornylmethanols and 2-azanorbornylmethanethiol as a catalyst

Optically active 2-azanorbornylmethanols and 2-azanorbornylmethanethiol were prepared from ethyl (1 S,3 S,4 R)-2-[( R)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate and catalyzed the enantioselective addition of diethylzinc to aldehydes to give optically active secondary alcohols. Chira...

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Published inTetrahedron: asymmetry Vol. 8; no. 9; pp. 1391 - 1401
Main Authors Nakano, Hiroto, Kumagai, Noriyuki, Matsuzaki, Hisao, Kabuto, Chizuko, Hongo, Hiroshi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 08.05.1997
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
ORGANOZINC REAGENTS
ALCOHOLS
ACID-DERIVATIVES
ASYMMETRIC-SYNTHESIS
BENZALDEHYDE
LIGANDS
REDUCTION
DIALKYLZINCS
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Summary:Optically active 2-azanorbornylmethanols and 2-azanorbornylmethanethiol were prepared from ethyl (1 S,3 S,4 R)-2-[( R)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate and catalyzed the enantioselective addition of diethylzinc to aldehydes to give optically active secondary alcohols. Chiral Ligands A, 2-Azanorbornylmethanols and 2-Azanorbornylmethanethiol, were prepared and catalyzed the addition of diethylzinc to aldehydes to furnish secondary alcohols in up to > 99%ee.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(97)00118-3