95581-22-9Relevant academic research and scientific papers
Stereoselectivity in the Hydride Reduction of Acyclic Diketones (1,2-, 1,3-, 1,4-, and 1,5-Induction)
Maier, Guenther,Roth, Cornelia,Schmitt, Reinhart K.
, p. 704 - 721 (2007/10/02)
Diketones 2, 5, 9, and 19 as well as hemiketal 22 react with lithium aluminum hydride to give mixtures of d,l- and meso-diols.The stereochemical assignment of the diols can be obtained either by direct comparison with authentic samples (1,2-diols) or by NMR differentiation of diastereotopic groups (1,3- and 1,5-diols) or by stereospecific cyclization to the sila-heterocycles 12 and 13 (1,4-diols).The 1,2- and 1,4-diketones preferably produce meso-diols, whereas 1,3- and 1,5-diketones mostly lead to d,l-isomers.These alternating stereoselectivities can be explained by a stepwise reduction generating complexes of types 24 - 27 which are attacked by excess hydride via a diastereoface differentiating mode.
