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Asymmetric Reduction of Ketones with NaBH 4 in the Presence of Lecithin
Author(s) -
Doiuchi Tohru,
Minoura Yuji
Publication year - 1976
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.197600017
Subject(s) - chemistry , ketone , alkyl , lecithin , micelle , optically active , aqueous solution , medicinal chemistry , organic chemistry , reduction (mathematics) , chromatography , geometry , mathematics
The heterogeneous reduction of various water‐insoluble ketones (i.e., alkyl phenyl ketones and alkyl methyl ketones) was carried out with an aqueous NaBH 4 solution in the presence of lecithin. It was found that the rate of the reduction reaction from ketone to carbinol was enhanced by lecithin, which is known as an optically active and zwitterionic surface active substance. Furthermore, when the unsymmetric ketones were reduced in this system the carbinols obtained were found to be optically active, though their optical yields were low. From the above results, it was concluded that the reduction reaction proceeds mainly at the micelle–water interface.