CIS-CONFIGURATIONS AND TRANS-CONFIGURATIONS OF ALPHA,ALPHA'-DISUBSTITUTED PIPERIDINES AND PYRROLIDINES BY GC-FTIR - APPLICATION TO DECAHYDROQUINOLINE STEREOCHEMISTRY

Authors
GARRAFFO HM SIMON LD DALY JW SPANDE TF JONES TH
Citation
Hm. Garraffo et al., CIS-CONFIGURATIONS AND TRANS-CONFIGURATIONS OF ALPHA,ALPHA'-DISUBSTITUTED PIPERIDINES AND PYRROLIDINES BY GC-FTIR - APPLICATION TO DECAHYDROQUINOLINE STEREOCHEMISTRY, Tetrahedron, 50(39), 1994, pp. 11329-11338
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
39
Year of publication
1994
Pages
11329 - 11338
Database
ISI
SICI code
0040-4020(1994)50:39<11329:CATOA>2.0.ZU;2-C
Abstract
GC-FTIR spectroscopy provides a convenient, rapid method to distinguis h cis- and trans-alpha,alpha'-disubstituted piperidines and pyrrolidin es; the pyrrolidines usually first require N-methylation. Cis-isomers exhibit significant Bohlmann bands, transisomers only very weak bands. The method is also applicable to alkaloids containing a piperidine ri ng. For example, a 2-propyl-5-methyldecahydroquinoline, named trans-19 5A, recently detected in skin extracts of a dendrobatid frog is shown by GC-FTIR to have C(2) and C(8a) in a cis-orientation,