Herein we describe an unprecedented B-(C6F5)(3)-catalyzed cascade reaction of N-allyl-N-furfurylamides involving an initial intramolecular furan Diels-Alder reaction and subsequent ether cleavage. The reaction has a broad substrate scope, even tolerating a trialkyl-substituted olefin as the dienophile, which has not previously been observed with conventional furan Diels-Alder reactions. In addition, the relative configuration of the product can be controlled by the choice of the silyl group: reactions involving Et3SiH and (Pr3SiH)-Pr-i gave different diastereomers. Control experiments and the computational studies revealed that the steric bulk of the silyl group plays a key role in determining the reaction pathway and thus the relative configuration of the product.