1312306-59-4Relevant articles and documents
Synthesis of α-amino acid derivatives and peptides via enantioselective addition of masked acyl cyanides to imines
Yang, Kin S.,Rawal, Viresh H.
supporting information, p. 16148 - 16151 (2015/02/02)
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.
