Chameleon catches in combinatorial chemistry: Tebbe olefination of polymer supported esters and the synthesis of amines, cyclohexanones, enones, methyl ketones and thiazoles

Abstract

Tebbe olefination of supported esters R¹CO₂CH₂–polymer gave the corresponding vinyl ethers R¹C(CH₂)OCH₂–polymer which were released, under acidic conditions, to produce methyl ketones R¹COMe; by reductive amination, to produce amines R¹CH(Me)NHR²; by bromination and reaction of R¹CBr(CH₂Br)OCH₂-polymer with thioureas to produce thiazoles; or, for supported dienyl ethers derived from α,β-unsaturated esters, by Diels–Alder reaction and acid mediated cleavage to produce cyclohexanone derivatives.