NMR studies of dextromethorphan in both isotropic and anisotropic states.

Abstract:

:Herein, we present the solution-state NMR studies on dextromethorphan (1) under both isotropic and anisotropic conditions. From the measurement of 22 residual dipolar couplings using a stretched polystyrene gel (PS), we show that accurate and detailed structural information is readily determined including the relative stereochemical assignments of chiral centers, validation of diastereomer configuration, and the stereospecific assignment of the seven pairs of prochiral protons. This utility of PS gels is thus showcased to obtain rapid, accurate conformational, and relative configuration information in this important class of compounds without recourse to X-ray analysis.

journal_name

Chirality

journal_title

Chirality

authors

Swarbrick JD,Ashton TD

doi

10.1002/chir.20703

subject

Has Abstract

pub_date

2010-01-01 00:00:00

pages

42-9

issue

1

eissn

0899-0042

issn

1520-636X

journal_volume

22

pub_type

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