Microwave-assisted ethylene-alkyne cross-metathesis: synthesis of chiral 2-(N-1-acetyl-1-arylmethyl)-1,3-butadienes

Chiral 1-arylpropargyl amides, which are resistant to undergoing ethylene-alkyne cross-metathesis at atmospheric pressure, were reacted under microwave irradiation to afford enantiomerically enriched 2-(N-1-acetyl-1- arylmethyl)-1,3-butadienes within a few minutes. Enantiomerically enriched amides underwent ethylene-alkyne cross-metathesis with retention of configuration at the propargylic/allylic position. A series of chiral 2-(N-1-acetyl-1-arylmethyl)-1,3-butadienes were synthesised with ee ≥95%; these latter compounds could be used as building blocks for the synthesis of new antifungal and antiaromatase agents. © 2005 Elsevier Ltd. All rights reserved.