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Extra info for Asymmetric Synthesis and Application of α-Amino Acids
This rationale is consistent with the observed solvent effects (Table IV, entries 1-3), since deprotonation of 27B via chelation of the Boc-carbonyl group with a metal cation (transition state Y, M=K) becomes more significant in less coordinative solvents, resulting in decreased enantioselectivity. Enantio selectivity in seven-membered ring formation depends on the reaction time (Table V , entries 8 and 9). This seems to be due to the partial racemization of a chiral enolate intermediate during relatively slow seven-membered-ring cyclization.
Org Biomol. Chem. 2006, 4, 3225-3227. (c) Nuzzi, A . ; Massi, A . ; Dondoni, A . QSAR Comb. Sci. 2007, 26, 1191-1199. (d) Marra, A . ; Vecchi, A . ; Dondoni, A . J. Org. Chem. 2008, 73, in press. Rostovtsev, V . V . ; Green, L. ; Fokin, V . V . ; Sharpless, K . B . Angew. Chem. Int. Ed. 2002, 41, 2596-2599. Tornøe, C. ; Meldal, M . J. Org Chem. 2002, 67, 30573062. (a) Kolb, H . ; Finn, M . ; Sharpless, K . B . Angew. Chem. Int. Ed. 2001, 40, 2004-2021. (b) Kolb, H . ; Sharpless, K . B. Drug Disc.
However, the most straightforward method for their synthesis would involve asymmetric a-alkylation of the parent a-amino acids without the aid of external chiral sources such as chiral auxiliaries or chiral catalysts. Since both L— and D-a-amino acids are readily commercially available, the synthetic route shown in Scheme 2 seems most attractive for the purpose. This process, however, usually gives racemic ct-alkylated products from either L - or D-a-amino acids because the enolate formation eliminates the chiral information at C(2) and an achiral enolate common to both L - and D-series is Scheme 1.