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
Chiralityjournal_title
Chiralityauthors
Swarbrick JD,Ashton TDdoi
10.1002/chir.20703subject
Has Abstractpub_date
2010-01-01 00:00:00pages
42-9issue
1eissn
0899-0042issn
1520-636Xjournal_volume
22pub_type
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