Build/couple/pair strategy combining the Petasis 3-component reaction with Ru-catalyzed ring-closing metathesis and isomerization

ACS Combinatorial Science
Erhad AscicThomas E Nielsen

Abstract

A "build/couple/pair" pathway for the systematic synthesis of structurally diverse small molecules is presented. The Petasis 3-component reaction was used to synthesize anti-amino alcohols displaying pairwise reactive combinations of alkene moieties. Upon treatment with a ruthenium alkylidene-catalyst, these dienes selectively underwent ring-closing metathesis reactions to form 5- and 7-membered heterocycles and cyclic aminals via a tandem isomerization/N-alkyliminium cyclization sequence.

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Citations

Dec 4, 2015·Organic & Biomolecular Chemistry·E LenciA Trabocchi
Jan 22, 2013·Angewandte Chemie·Nitin T PatilBalasubramanian Sridhar
Jun 14, 2014·Chemistry : a European Journal·Mette Ishoey, Thomas E Nielsen
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Feb 6, 2015·Organic Letters·Thanaphat Thaima, Stephen G Pyne
Jan 19, 2013·The Journal of Organic Chemistry·Igor DubovykAndrei K Yudin
Apr 5, 2013·Organic Letters·Mette T Petersen, Thomas E Nielsen
Aug 28, 2019·Chemical Reviews·Peng WuThomas E Nielsen

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