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.