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Nitrile Oxide versus Nitrone – Switching Regioselectivity of Intramolecular 1,3‐Dipolar Cycloadditions towards the Preparation of Aminopiperidinecarboxylates
Author(s) -
Würdemann Martina,
Christoffers Jens
Publication year - 2013
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.201301039
Subject(s) - chemistry , isoxazole , nitrone , nitrile , intramolecular force , regioselectivity , cycloaddition , amination , 1,3 dipolar cycloaddition , combinatorial chemistry , reductive amination , piperidine , organic chemistry , stereochemistry , catalysis
3‐(Allylamino)‐ and 3‐(propargylamino)propanal were converted via the corresponding oximes into nitrile oxides, which readily underwent intramolecular 1,3‐dipolar cycloadditions to furnish a piperidine‐annulated isoxazole or isoxazoline. The annulated isoxazoline was transformed into orthogonally carbamate‐protected cis ‐ and trans ‐4‐aminopiperidine‐3‐carboxylates, both representing interesting scaffolds for combinatorial chemistry. Through sequences of amidations and deprotections two triply functionalized products were obtained as examples for diversification. After Boc removal, the piperidino‐annulated isoxazole was also subjected to diversifying reactions, such as reductive amination, amidation, and the formation of sulfonamido‐ and ureido‐substituted derivatives.