@article{TEXTUAL, recid = {13390}, author = {Yang, Kin S. and Rawal, Viresh H.}, title = {Synthesis of α-Amino Acid Derivatives and Peptides via Enantioselective Addition of Masked Acyl Cyanides to Imines}, journal = {Journal of the American Chemical Society}, address = {2014-11-07}, number = {TEXTUAL}, abstract = {A general, asymmetric synthesis of amino acid derivatives is reported. Masked acyl cyanide (MAC) reagents are shown to be effective umpolung synthons for enantioselective additions to N-Boc-aldimines. The reactions are catalyzed by a modified cinchona alkaloid, which can function as a bifunctional, hydrogen bonding catalyst, and afford adducts in excellent yields (90–98%) and high enantioselectivities (up to 97.5:2.5 er). Unmasking the addition products gives acyl cyanide intermediates that are intercepted by a variety of nucleophiles to afford α-amino acid derivatives. Notably, the methodology provides an alternative method for peptide bond formation.}, url = {http://knowledge.uchicago.edu/record/13390}, }