First regioselective ring opening of serine derived cyclic sulfamidate by hard nucleophiles like ArONa is developed, where β-elimination of serine sulfamidate ester by stronger nucleophiles is overcome by reversal of the electronic effect of the carboxylate anion. This method provides easy and direct access to a variety of N-Boc- and N-PMB protected β-aryloxy-α-amino acids with complete retention of enantiopurity in moderate to high yields.
A highly enantioselective (up to 91% ee) rhodium-catalyzed asymmetric addition of arylboronic acids has been achieved leading to the challenging dihydro-3-nitronaphthalenes using one equivalent of phosphoramidite ligand to rhodium catalyst. A concise formal asymmetric synthesis of the dopamine D1 agonist, dihydrexidine was accomplished using the method.
First asymmetric synthesis of towards doxanthrine is accomplished with high diastereo- and enantioselectivity from β-aryloxyamino acid derived from D-serine.
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