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Synthesis of Triazolyl‐Substituted 3‐Aminopiperidines by Huisgen‐1,3‐Dipolar Cycloaddition – New Scaffolds for Combinatorial Chemistry
Author(s) -
Schramm Heiko,
Saak Wolfgang,
Hoenke Christoph,
Christoffers Jens
Publication year - 2010
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/ejoc.200901458
Subject(s) - chemistry , cycloaddition , aziridine , piperidine , 1,3 dipolar cycloaddition , click chemistry , ring (chemistry) , sequence (biology) , combinatorial chemistry , stereochemistry , polymer chemistry , organic chemistry , catalysis , biochemistry
Orthogonally N ‐protected (Boc and Cbz) 4‐(1,2,3‐triazol‐4‐yl)‐substituted 3‐aminopiperidines are new scaffolds for combinatorial chemistry. They were prepared from a piperidine building block by a sequence of nucleophilic aziridine ring opening with NaN 3 and subsequent copper‐catalyzedHuisgen 1,3‐dipolar cycloaddition with ten different alkynes. Constitution and relative configuration of the major as well as minor products were established by single‐crystal X‐ray structure analysis of bromophenylsulfonyl derivatives.