TiCl4-mediated reduction of 1,3-diketones with BH3-pyridine complex: a highly diastereoselective method for the synthesis of syn-1,3-Diols
[reaction: see text] 1,3-Diketones can be reduced in high yields and with excellent diastereoselectivity to the corresponding syn-1,3-diols by carrying out the reaction with BH3-pyridine complex in CH2Cl2 at -78 degrees C in the presence of an equivalent of TiCl4 and 0.1 equiv of pyridine. This protocol shows a general character: excellent results are obtained when the groups bound to the carbonylic functions are linear or branched carbon chains and aromatic or benzylic frameworks as well.
Bartoli
G
Dipartimento di Chimica Organica A. Mangini, Bologna, Italy. bartoli@ms.fci.unibo.it
Bosco
M
Bellucci
MC
Dalpozzo
R
Marcantoni
E
Sambri
L