A rare case of facial selectivity inversion for Sharpless asymmetric dihydroxylation in a series of structurally homogeneous substrates: synthesis of non-racemic 3-(nitrophenoxy)-propane-1,2-diols
作者:Zemfira A. Bredikhina、Alexey V. Kurenkov、Olga A. Antonovich、Alexander V. Pashagin、Alexander A. Bredikhin
DOI:10.1016/j.tetasy.2014.05.008
日期:2014.7
Asymmetric dihydroxylation of mono nitrophenyl allyl ethers leads to the corresponding non-racemic 3-(nitrophenoxy)-propane-1,2-diols 1a-c. As this takes place, regardless of the reagent used (AD-mix-alpha or AD-mix-beta), the configuration of the predominant enantiomer for the para- and meta-nitrosubstituted products is opposite to the configuration of the ortho-nitrophenyl derivative. A correlation between the melting points and vibrational spectra of the racemic and enantiopure diols 1a-c allowed us to establish that all of the chiral substances investigated formed stable racemic compounds in the solid phase. (C) 2014 Elsevier Ltd. All rights reserved.