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Solid‐Phase Synthesis of Piperidines by N ‐Acyliminium Ion Chemistry
Author(s) -
Veerman Johan J. N.,
Klein Jasper,
Aben René W. M.,
Scheeren Hans W.,
Kruse Chris G.,
van Maarseveen Jan H.,
Rutjes Floris P. J. T.,
Hiemstra Henk
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200209)2002:18<3133::aid-ejoc3133>3.0.co;2-h
Subject(s) - chemistry , benzotriazole , nucleophile , solid phase synthesis , ring (chemistry) , ion , combinatorial chemistry , carbamate , organic chemistry , medicinal chemistry , stereochemistry , catalysis , peptide , biochemistry
An efficient solid‐phase procedure for the synthesis of a number of 2‐substituted piperidines is reported. Starting from solid‐supported carbamate‐tethered δ‐amino acetals, 2‐benzotriazolyl‐substituted (Bt‐substituted) piperidines were obtained by acid‐induced ring‐closure followed by trapping of the transient N ‐acyliminium ions with benzotriazole. These 2‐Bt‐substituted piperidines were then used as precursors for the successful introduction of several C ‐nucleophiles by N ‐acyliminium ion chemistry. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)