The synthesis of Fmoc- O-allyl β-serine

Abstract

Two concise routes for the synthesis of the title amino acid have been developed. The first route employs Seebach’s general approach [Seebach, D.; Lelais, G.; Micuch, P.; Josien-Lefebvre, D.; Rossi, F. Helv. Chim. Acta 2004, 87, 3131] with Arndt Eistert homologation of Boc- O-allyl α-serine as the key process. The second route employs an approach using Boc-α-aspartic acid as a starting material [Salzmann, T.N.; Ratcliffe, R.W.; Christensen, B.G.; Bouffard, F.A. J. Am. Chem. Soc. 1980, 102, 6163; Rodriguez, M.; Llinares, M.; Doulut, S.; Heitz, A.; Martinez, J. Tetrahedron. Lett. 1991, 32, 923] with a selective palladium-catalysed O-allylation [Haight, A.R; Stoner, E.J.; Peterson, M.J.; Grover, V.K. J. Org. Chem. 2003, 68, 8092] as key processes. These two routes are evaluated for their relative efficiency and safety.