Meng-Yang Chang

Reaction of different α-sulfonyl acetamides with methyl acrylate

The base-induced tandem-coupling/cyclization reactions of various α-sulfonyl acetamide derivatives A with methyl acrylate differentiated between two different pathways to form α-sulfonyl analogs of glutarimides B and 2-hydroxycyclohexenecarboxylic acid derivatives C in different ratios. The reaction of α-sulfonyl acetamide dianion with methyl acrylate depended on three factors: the stability of the dianion, concentration of methyl acrylate and the structure of sufonyl and amide substituents. By changing the reaction conditions, we efficiently controlled the cycloaddition reaction to synthesize the desired product, each of which has potential biological activities. A ring closure mechanism is proposed for the reactions.

New synthesis of 3-aryl-N-n-propyl-piperidines

The synthesis of 3-aryl-N-n-propyl-piperidines is described in six steps starting from α-sulfonyl acetamide via the formal [3+3] cycloaddition reaction of the latter into glutarimide. The pathway involves an efficient cycloaddition and regioselective reduction, and yields useful building blocks for heterocyclic chemistry.

A Synthesis of Racemic Thalidomide

Abstract A synthesis of racemic thalidomide is described using formal [3+3] cycloaddition strategy as the key step. The total yield of thalidomide was 30% in three steps from ester 2.