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A Mechanistic Aspect of the Remote Asymmetric Transmission Observed During Substrate Reduction with Chiral NADH Model Compounds
Author(s) -
Baba Naomichi,
Hoshide Fumitoshi,
Oda Jun'Ichi,
Inouye Yuzo
Publication year - 1985
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198500037
Subject(s) - chemistry , stereospecificity , substituent , yield (engineering) , amide , asymmetric induction , substrate (aquarium) , stereochemistry , reduction (mathematics) , organic chemistry , enantioselective synthesis , catalysis , materials science , oceanography , geometry , mathematics , geology , metallurgy
Asymmetric reduction of ethyl benzoylformate were conducted using chiral NADH model compounds with various substituents at the 3‐ and N 1 ‐positions of the dihydronicotinamide. In one case, in which l‐prolinamide resides at the terminal of the N 1 ‐substituent, the optical yield was 90%; the remote asymmetric induction was ascribed to a stereospecific blockage of one of the diastereotopic faces in the dihydronicotinamide by an interaction of the amide functions with magnesium.