CHEMOSELECTIVE CONVERSION OF CONJUGATED NITROALKENES INTO KETONES BY SODIUM BOROHYDRIDE-HYDROGEN PEROXIDE - A NEW SYNTHESIS OF 4-OXOALKANOIC ACIDS, DIHYDROJASMONE AND (+ -)-EXO-BREVICOMIN/
R. Ballini et G. Bosica, CHEMOSELECTIVE CONVERSION OF CONJUGATED NITROALKENES INTO KETONES BY SODIUM BOROHYDRIDE-HYDROGEN PEROXIDE - A NEW SYNTHESIS OF 4-OXOALKANOIC ACIDS, DIHYDROJASMONE AND (+ -)-EXO-BREVICOMIN/, Synthesis, (7), 1994, pp. 723-726
A new, simple, cheap, and practical procedure for the direct transform
ation of alpha,beta-unsaturated nitroalkenes into ketones has been rea
lized by the NaBH4/H2O2 system. By this method, other functional group
s such as C-C double bonds, ketals or aromatic nitro groups were prese
rved. Application of this methodology to the preparation of 4-oxoalkan
oic acids, dihydrojasmone, and (+/-)-exo-brevicomin is also reported.