Chiral β- and γ-aminoalcohols derived from (+)-camphor and (−)-fenchone as catalysts for the enantioselective addition of diethylzinc to benzaldehyde

The addition of Me 3SiCN and LiCH 2CN to (+)-camphor and (−)-fenchone, respectively, followed by reduction leads to chiral β- and γ-aminoalcohols. The enantioselectivities realized using these aminoalcohols as ligands in the addition of Et 2Zn to benzaldehyde were lower than those obtained using the...

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Published inTetrahedron: asymmetry Vol. 12; no. 9; pp. 1323 - 1329
Main Authors Dimitrov, Vladimir, Dobrikov, Georgi, Genov, Miroslav
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 11.06.2001
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
ORGANIC-SYNTHESIS
AUXILIARIES
AMINO-ALCOHOLS
REAGENTS
ASYMMETRIC INDUCTION
DIALKYLZINCS
ALKYLATION
CERIUM(III) CHLORIDE
ALDEHYDES
1,4-AMINOALCOHOLS
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Summary:The addition of Me 3SiCN and LiCH 2CN to (+)-camphor and (−)-fenchone, respectively, followed by reduction leads to chiral β- and γ-aminoalcohols. The enantioselectivities realized using these aminoalcohols as ligands in the addition of Et 2Zn to benzaldehyde were lower than those obtained using the corresponding δ-aminoalcohols. New chiral β- and γ-aminoalcohols were synthesized by diastereoselective addition of Me 3SiCN and LiCH 2CN to (+)-camphor and (−)-fenchone followed by LiAlH 4 reduction. The enantioselectivities achieved by using these aminoalcohols as ligands in the addition of Et 2Zn to benzaldehyde are lower than those obtained with the corresponding δ-aminoalcohols.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(01)00221-X