Journal of the American Chemical Society p. 6709 - 6716 (1984)
Update date:2022-08-11
Topics:
Noyori
Tomino
Tanimoto
Nishizawa
A new chiral hydride reagent, BINAL-H, has been devised by the modification of lithium aluminum hydride with equimolar amounts of (R)- or (S)-2,2 prime -dihydroxy-1,1 prime -binaphthyl and a simple alcohol. This reducing agent exhibits exceptionally high enantioface-differentiating ability in the reduction of prochiral alkyl phenyl ketones in tetrahydrofuran. The phenyl and alkyl groups attached to the carbonyl function are differentiated primarily by the difference in electronic properties rather than the relative bulkiness. A six-membered-ring transition-state model is proposed to account for the stereochemical consequences. This mechanism is consistent with the phenomena observed with other unsaturated carbonyl substrates.
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