Direct peptide coupling of novel amino acid derivatives produced by rearrangement of catalytically generated ammonium ylides

JS Clark, MD Middleton

Index: Clark, J. Stephen; Middleton, Mark D. Tetrahedron Letters, 2003 , vol. 44, # 37 p. 7031 - 7034

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Citation Number: 5

Abstract

Protected amino acids can be prepared from substrates in which a diazo ester is aryl- tethered to an allylic amine, by catalytic intramolecular ammonium ylide generation and [2, 3] rearrangement. When the aryl tether is sufficiently electron-deficient, direct coupling of the rearrangement product with a hindered amino acid ester to give a dipeptide is possible, and ammonium ylide generation, rearrangement and peptide coupling can be accomplished ...