Categories: C-C Bond Formation > Oxygen-containing molecules >
Synthesis of 1,2-diols
Lithiated epoxides react stereospecifically with boronates to give syn-1,2-diols, a process that can be used iteratively to create triols containing four stereogenic centers.
E. Vedrenne, O. A. Wallner, M. Vitale, F. Schmidt, V. K. Aggarwal, Org. Lett., 2009, 11, 165-168.
Usually, silyl-protected α-hydroxy aldehydes undergo Felkin addition due to steric and eletronic properties of the silyl group. However, dialkylzincs, functionalized dialkylzincs, and vinylzinc reagents add to silyl-protected α-hydroxy aldehydes with high selectivity for chelation-controlled or anti-Felkin products in the presence of alkylzinc halides or triflates.
G. R. Stanton, C. N. Johnson, P. J. Walsh, J. Am. Chem. Soc., 2010, 132, 4399-4408.
A catalytic enantioselective diboration of vinyl boronate esters furnishes chiral tris(boronates). Subsequent intermolecular or intramolecular deborylative alkylation occurs in a diastereoselective fashion.
J. R. Coombs, L. Zhang, J. P. Morken, J. Am. Chem. Soc., 2014, 136, 16140-16143.
A nickel(0) N-heterocyclic carbene complex-catalyzed coupling of α-silyloxy aldehydes and alkynylsilanes provides an effective entry to various anti-1,2-diols with excellent diastereoselectivity.
K. Sa-ei, J. Montgomery, Org. Lett., 2006, 8, 4441-4443.