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Catalytic enantioselective addition of diethylzinc to (hetero)aromatic aldehydes

✍ Scribed by Irina Iovel; Günther Oehme; Edmunds Lukevics

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
92 KB
Volume
12
Category
Article
ISSN
0268-2605

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✦ Synopsis

The asymmetric alkylation with diethylzinc of five heterocyclic aldehydes and benzaldehyde (for comparison) has been studied in the presence of two optically active amino alcohols: (S)-2-amino-1-butanol (AB) and (1S,2R)-N,Ndibutylnorephedrine (DBNE). A number of chiral (hetero)aromatic secondary alcohols were synthesized in high yields (95-98%) with enantioselectivity up to 92% enantiomeric excess (ee) in the presence of DBNE catalyst. Optically active thienyl and 4-pyridyl derivatives were prepared for the first time by catalytic asymmetric alkylation. The influence of the amount of DBNE on the enantioselectivity was investigated. In contrast to benzaldehyde, 2-furan-and 2thiophene-carbaldehydes, in the case of 3-and 4pyridinecarbaldehydes the ee values depend directly on the catalyst concentration.

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