Abstract
The catalytic intramolecular and intermolecular α-amidoalkylation of deactivated N,O-acetals equipped with either two ester groups or both an ester and a cyano groups α to the reactive center has been developed. Reactions in the cyano ester series proceeded under harsher reaction conditions than those in the diester series, but furnished products with two contiguous quaternary and tertiary stereocenters with high to complete diastereocontrol. The reactivity trends and stereoselectivity profiles exhibited by these reactions may be consistent with a relay mode exerted by the ester arm(s), which might possibly direct the catalyst delivery and/or stabilize the raising carbenium ion through anchimeric bridging.
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