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Cis- and trans-configurations of α,α′-disubstituted piperidines and pyrrolidines by GC-FTIR; application to decahydroquinoline stereochemistry

✍ Scribed by H. Martin Garraffo; Lara D. Simon; John W. Daly; Thomas F. Spande; Tappey H. Jones

Book ID: 104204696
Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 713 KB
Volume: 50
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)89276-0

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✦ Synopsis

GC-FTR spectroscopy provides a convenient, rapid method to distinguish cis-and transit,a'disubstituted piperidines and pyrrolidines; the pyrroIicIInes usuaIIy first require N-methylation. Cis-isomers exhibit significant BobImauu bands. tram-isomers only very weak bands. The method is also applicable to aIkaIoids containing a piperkkue ring. For example, a 2-propyl-S-methyldecahydroquInoIine, named trans-195A, recently detected in skin extracts of a dendrobatid frog is shown by GC-FITR to have C(2) and C(8a) In a cts+rIentation.

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