Enantioselective addition of diethylzinc to benzaldehyde catalyzed by a small amount of chiral 2-amino-1-alcohols
β Scribed by Nobuki Oguni; Takao Omi
- Publisher
- Elsevier Science
- Year
- 1984
- Tongue
- French
- Weight
- 103 KB
- Volume
- 25
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
The reaction of diethylzinc with benzaldehyde catalyzed by a small amount of chiral 2-amino-l-alcohols in toluene at room temperature gave optically active 1-phenylpropan-l-01 almost quantitatively in 2 50% ee.
Asymmetric alkylation of various aldehydes with organometallic reagents in the presence of chiral organic reagents has been recently developed and high ee was attained in some cases'.
In order to attain high optical yield in the reported systems, the use of a stoichiometric amount of chiral reagents and to run the reaction at very low temperature of -llOe-120Β°C are essential.
Very recently we reported that chiral catalysis by transition metal complexes of d-camphorquinonedioxime in the reaction of diethylzinc with arylaldehydes gave optically active alcohols almost quantitatively in 40 -60% ee at room temperature2. The reaction was based
π SIMILAR VOLUMES
Co(acac) 2 in the presence of chiral ligands has been employed as catalyst for the enantioselective conjugate addition of diethylzinc to chalcone. With chiral amino alcohols derived from (+)-camphor, enantioselectivities up to 83% were achieved.
Optically active ferrocenyl amino alcohols have been prepared from commercially available l-alaninol and l-leucinol. They have been used in catalytic amounts as chiral ligands in the addition of diethylzinc to benzaldehyde. 1-Phenylpropanol has thus been obtained in up to 95% enantiomeric excess.
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