Determination of relative stereochemistry

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This review article discusses use of ^2,3J_CH, ³J_HH scalar couplings and ¹³C chemical shifts for assignment of relative stereochemistry of centers (marked in bold) in -CHX-CHY- and -CHX-CH₂-CHY- hydrocarbon fragments, where X and Y are polar substituents.

²J_CH couplings are useful in fragments CYH-CHX where substituent X is polar (and the coupling between atoms marked in bold is observed).

Bifulco, G., Dambruoso, P., Gomez-Paloma, L., Riccio, R.. Determination of Relative Configuration in Organic Compounds by NMR Spectroscopy and Computational Methods

Chem Rev 107(9):3744--79, 2007

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The article below is the pioneering work showing that CH and HH coupling constants can be used to determine relative stereochemistry of two adjacent stereocenters in acyclic hydrocarbons. The analysis is based on assumption that most acyclic hydrocarbons substituted with -OH, -OCH₃, -CH₃ and other non-bulky substituents favor gauche or anti conformations within 10^o accuracy.

Matsumori, N., Kaneno, D., Murata, M., Nakamura, H., Tachibana, K.. Stereochemical determination of acyclic structures based on carbon-proton spin-coupling constants. A method of configuration analysis for natural products

J. Org. Chem 64(3):866--876, 1999

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