Categories: C-C Bond Formation > Oxygen-containing molecules >
Synthesis of 1,2-diols
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Recent Literature
A catalytic enantio- and diastereoselective addition of alkyl 1,1-diboron
reagents to aryl and vinyl aldehydes provides 1,2-hydroxyboronates promoted by a
readily available chiral monodentate phosphoramidite-copper complex. Products
contain two contiguous stereogenic centers and are obtained in good yield, good
d.r., and high e.r. The 1,2-hydroxyboronate products can be transformed into
versatile derivatives.
M. V. Joannou, B. S. Moyer, S. J. Meek, J. Am. Chem. Soc., 2015,
137, 6176-6179.
A one-pot, selective cross pinacol-type coupling between two structurally
similar aromatic aldehydes in the presence of low-valent titanium gave
unsymmetrical pinacols in good yields and diastereoselectivities. This synthetic
methodology, which is based on the affinity of the substituents to the surface
of titanium, significantly extends the scope of the cross pinacol-type couplings.
X.-F. Duan, J.-X. Feng, G.-F. Zi, Z.-B. Zhang, Synthesis, 2009,
277-282.
A tandem Wittig Rearrangement/aldol reaction of O-benzyl or O-allyl
glycolate esters generates two carbon-carbon bonds and two contiguous
stereocenters with excellent diastereoselectivity in a single step from
simple starting materials. The [1,2]-Wittig rearrangement proceeds under
very mild reaction conditions.
M. B. Betrand, J. P. Wolfe, Org. Lett.,
2006,
8, 4661-4663.