Lyndon C. Xavier

Preparation of 2-aryl- and 2-alkenyl-substituted carbapenems under mild suzuki cross-coupling conditions

Abstract An extraordinarily mild procedure for the synthesis of 2-aryl- and 2-alkenyl-substituted carbapenems via palladium-catalyzed coupling of a vinyl triflate with aryl or vinyl boronic acids is described. A major advantage of this procedure is the use of nontoxic boronic acid intermediates in place of highly toxic organostannane compounds which are used in the corresponding Stille cross-coupling reactions.

In situ NMR spectroscopic studies of aniline ortho acylation (“sugasawa reaction”): The nature of reaction intermediates and Lewis acid influence on yield

Abstract Ortho acylation of anilines by nitriles in the presence of BCl 3 and a second Lewis acid appear to proceed through an intermediate “supercomplex” including all four components. Yield improvements were obtained based on recognition that chloride affinity of the second Lewis acid governs supercomplex formation. Aniline protonation was found to be the cause of incomplete reaction.

Synthesis of a new generation reverse transcriptase inhibitor via the BCl3/GaCl3-induced condensation of anilines with nitriles (sugasawa reaction)

Abstract The synthesis of 1 was achieved in high overall yield through a mechanism-based improvement of the preparation of o-acyl anilines.