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Catalyzed Enantioselective Alkylation of Aldehydes
Author(s) -
Bolm Carsten,
Schlingloff Gunther,
Harms Klaus
Publication year - 1992
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19921250529
Subject(s) - diethylzinc , chemistry , enantioselective synthesis , alkylation , steric effects , catalysis , stereoselectivity , organic chemistry , optically active , medicinal chemistry
Enantioselective alkylation of a variety of aldehydes with diethylzinc was achieved by using catalytic amounts of optically active pyridines and C 2 ‐symmetric 2,2′‐bipyridines. The products were obtained in good yields with high enantioselectivities. Steric factors of the catalyst structure which govern the stereoselectivity were revealed, and important reaction intermediates were identified by spectroscopic means and singlecrystal X‐ray diffraction. The effect of additives on the optical purity of the product was studied. A strong asymmetric amplification was found with catalysts of low ee′s.