ACS Combinatorial Science 2012-04-09

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

Erhad Ascic, Sebastian T Le Quement, Mette Ishoey, Mathilde Daugaard, Thomas E Nielsen

Index: ACS Comb. Sci. 4th ed., 14 , 253-257, (2012)

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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.