An Enyne Cope Rearrangement Enables Polycycloalkane Synthesis from Readily Available Starting Materials | Zendy

Scott Sarah K. | Zendy; Grenning Alexander J. | Zendy

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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.

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