Ontology highlight
ABSTRACT:
SUBMITTER: Banert K
PROVIDER: S-EPMC6271402 | biostudies-literature | 2014 Sep
REPOSITORIES: biostudies-literature
Molecules (Basel, Switzerland) 20140905 9
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 aldehydes to yield polycyclic products 3b-d, orthoesters 4a-c, ketones 5 or epoxides 6a,b, respectively. Treatment of bis(trimethylsilyl) acetylenedicarboxylate (1c) with cyclooctyne leads to the ketone 7 v ...[more]