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An Enyne Cope Rearrangement Enables Polycycloalkane Synthesis from Readily Available Starting Materials
Author(s) -
Scott Sarah K.,
Grenning Alexander J.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201703186
Subject(s) - propargyl , enyne , electrophile , cope rearrangement , chemistry , adduct , knoevenagel condensation , cyclohexanone , organic chemistry , combinatorial chemistry , catalysis
Cyclohexanone‐derived Knoevenagel adducts (cyclohexylidenemalononitriles) and two different propargyl electrophiles serve as carbon sources for assembling diverse 6/7/5 tricycloalkanes, a common terpenoid framework. The sequence involves three unique reactions: 1) deconjugative propargylation, 2) one‐pot enyne Cope rearrangement/deconjugative propargylation, and 3) an allenic Pauson–Khand reaction.