Tandem Addition/Cyclization Reaction of Organozinc Reagents to 2-Alkynyl Aldehydes: Highly Efficient Regio- and Enantioselective Synthesis of 1,3-Dihydroisobenzofurans and Tetrasubstituted Furans

Abstract

The enantioselective addition of organozinc reagents to some 2-alkynyl benzaldehydes and the subsequent regioselective cyclization step was performed in one pot to form chiral 1,3-dihydroisobenzofurans with good product yields and excellent regio- and enantioselectivities. In the case of 2-alkynylcycloalkene aldehydes, tetrasubstituted furans were obtained in good product yields through a 1, 5-hydride shift of the preformed cyclization product.