Meso and dl diastereomers: Synthesis and 1H NMR study of the 1,3-diphenylpropane-1,3-diols. An advanced undergraduate project in physical organic chemistry

Abstract

Proton Magnetic Resonance. An integrated laboratory project that gives students an experimental approach to diastereomerism in molecular structure and to first- and second-order NMR spectroscopic analysis.

A Highly Diastereoselective TiCl4-Mediated Reduction of β-Hydroxy Ketones with BH3·py — A Very Efficient and General Synthesis of syn-1,3-Diols

“…[12] The spectroscopic data of the known compounds 1a, [1f] 1b, [1f] 1l, [1e] 1m, [13] 5a, [14] 5b, [15] 8a, [16] 8b, [17] 3b, [18] 3l, [1e] 3m, [19] 3o, [19] 1,2-syn-and 2,3-syn-7a, [7a] 1,2-syn-and 2,3-syn-7b, [7a] 1,2-syn-and 2,3-anti-10a, [7a] 1,2-anti-and 2,3-anti-10a, [7a] 1,2-syn-2 and 3-anti-10b, [7a] and 1,2-anti-2 and 3-anti-10b [7a] were identical to those reported in the literature.…”

Using NMR To Probe the Regio- and Stereochemistry of the Hydration of 1-Hexene

“…1 H and 13 C NMR spectra of samples from each reaction are then obtained 2. Because diastereomers are expected to display distinct NMR spectral patterns , , the composition of the diastereomeric mixtures from each reaction is analyzed by 1 H and 13 C NMR spectroscopy and compared. The results lead to a postlab discussion of NMR spectroscopic analysis of enantiomers and diastereomers, stereochemical relationships between faces of planar species such as carbocations and alkenes, and the effect of a chiral auxiliary , on a racemate.…”

Determination of absolute configuration of the phosphonic acid moiety of fosfazinomycins

“…First trials were performed using the racemic diol (±)-14, which was readily available. 24 Transesterification proceeded quantitatively within 1.5 h at room temperature in pyridine as judged by NMR spectroscopy (Scheme 4).…”