A case of remote asymmetric induction in the peptide-catalyzed desymmetrization of a bis (phenol)

…, J Balsells, D Pollard, J Murry, RA Reamer…

Index: Lewis, Chad A.; Gustafson, Jeffrey L.; Chiu, Anna; Balsells, Jaume; Pollard, David; Murry, Jerry; Reamer, Robert A.; Hansen, Karl B.; Miller, Scott J. Journal of the American Chemical Society, 2008 , vol. 130, # 48 p. 16358 - 16365

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Citation Number: 53

Abstract

We report a catalytic approach to the synthesis of a key intermediate on the synthetic route to a pharmaceutical drug candidate in single enantiomer form. In particular, we illustrate the discovery process employed to arrive at a powerful, peptide-based asymmetric acylation catalyst. The substrate this catalyst modifies represents a remarkable case of desymmetrization, wherein the enantiotopic groups are separated by nearly a full ...