β-Lactams derived from phenylalanine and homologues: effects of the distance between the aromatic rings and the α-stereogenic reactive center on the memory of chirality

descriptionPublicationkeyboard_double_arrow_right Article 01 Aug 2006 English Publisher:Elsevier BVJournal:Tetrahedron Letters, volume 47, pages 5,883-5,887 (issn: 0040-4039,

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Authors: Bonache de Marcos, María Ángeles; Cativiela, Carlos; García-López, M. Teresa; González-Muñiz, Rosario;

doi: 10.1016/j.tetlet.2006.06.057

handle: 10261/19700

β-Lactams derived from phenylalanine and homologues: effects of the distance between the aromatic rings and the α-stereogenic reactive center on the memory of chirality

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Abstract

The enantioselectivity in the base-promoted cyclization of N-chloroacetyl derivatives of Phe, Phg, and Hph is dependent on the side-chain length, with the best results for Phg analogues (up to 74% ee). In contrast, shortening of the N-substituent, from a (p-methoxy)benzyl group to a (p-methoxy)phenyl moiety, led to a decrease in selectivity.

This work was supported by CICYT (SAF 2003-07207- C02). M.A.B. thanks a post-grade fellowship from the CSIC (I3P).

5 pages, 1 table, 2 schemes.

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