35786-18-6Relevant academic research and scientific papers
A short approach to trisubstituted γ-butyrolactones
Dias, Luiz C.,De Castro, Ilton B. D.,Steil, Leonardo J.,Augusto, Tatiana
, p. 213 - 216 (2006)
The dihydroxylation of unsaturated aldol adducts with catalytic OsO 4 and NMO occurs under very mild conditions and with moderate to excellent levels of diastereoselectivity to give trisubstituted γ-butyrolactone derivatives.
Dihydroxylation-based approach for the asymmetric syntheses of hydroxy-γ-butyrolactones
Peed, Jennifer,Davies, Iwan R.,Peacock, Lucy R.,Taylor, James E.,Kociok-Koehn, Gabriele,Bull, Steven D.
experimental part, p. 543 - 555 (2012/02/04)
A method of preparing enantiopure hydroxy-γ-butyrolactones containing multiple contiguous stereocenters in high yield with good diastereoselectivity has been developed. Osmium tetroxide mediated dihydroxylation of a range of β-alkenyl-β-hydroxy-N-acyloxazolidin-2-ones results in formation of triols that undergo spontaneous intramolecular 5-exo-trig cyclization reactions to provide hydroxy-γ-butyrolactones. The stereochemistry of these hydroxy-γ-butyrolactones has been established using NOE spectroscopy, which revealed that 1-substituted, 1,1-disubstituted, (E)-1,2-disubstituted, (Z)-1,2-disubstituted, and 1,1,2-trisubstituted alkenes undergo dihydroxylation with anti-diastereoselectivity, while 1,2,2-trisubstituted systems afford syn-diastereoisomers. The synthetic utility of this methodology has been demonstrated for the asymmetric synthesis of the natural product 2-deoxy-d-ribonolactone. Published 2011 by the American Chemical Society.
