Synthesis with Perfect Atom Economy: Generation of Furan Derivatives by 1,3-Dipolar Cycloaddition of Acetylenedicarboxylates at Cyclooctynes

Synthesis with Perfect Atom Economy: Generation of Furan Derivatives by 1,3-Dipolar Cycloaddition of Acetylenedicarboxylates at Cyclooctynes

Cyclooctyne and cycloocten-5-yne undergo, at room temperature, a 1,3-dipolar cycloaddition with dialkyl acetylenedicarboxylates 1a,b to generate furan-derived short-lived intermediates 2, which can be trapped by two additional equivalents of 1a,b or alternatively by methanol, phenol, water or aldeh...

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Bibliographic Details
Main Authors: Klaus Banert, Sandra Bochmann, Andreas Ihle, Oliver Plefka, Florian Taubert, Tina Walther, Marcus Korb, Tobias Rüffer, Heinrich Lang
Format: Article
Language:English
Published: MDPI AG 2014-09-01
Series:Molecules
Subjects:
cascade reactions
cyclopropenes
Diels-Alder reactions
dipolar intermediates
epoxides
orthoesters
oxygen heterocycles
reaction mechanisms
retro-Brook reactions
strained compounds
Online Access:http://www.mdpi.com/1420-3049/19/9/14022

Internet

http://www.mdpi.com/1420-3049/19/9/14022

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