Tetrahedron: Asymmetry

Differentiation and assignment of the proton NMR signals in the bis-MTPA ester of meso-α, α′-dimethyl-1, 4-benzenedimethanol

BW Baldwin, CJ Morrow

Index: Baldwin, Bruce W.; Morrow, Cary J. Tetrahedron Asymmetry, 1996 , vol. 7, # 10 p. 2871 - 2878

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Citation Number: 5

Abstract

NaBH4 reduction of one ketone in 1, 4-diacetylbenzene followed by Amano PS catalyzed acylation of the R enantiomer, separation of the R acetate from the S alcohol, and reduction of the remaining ketone in each with NaBD4 has provided two mixtures of monodeuterated diol diastereomers: R, R (d) plus R, S (d) and S, R (d) plus S, S (d). Conversion of the unseparated diols into their bis-(R)-MTPA (mosher's) esters has allowed the NMR signals ...