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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

AuthorsBonache de Marcos, María Ángeles ; Cativiela, Carlos ; García-López, M. Teresa ; González-Muñiz, Rosario
Issue DateAug-2006
CitationTetrahedron Letters 47(··): 5883-5887 (2006)
AbstractThe 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.
Description5 pages, 1 table, 2 schemes.
Publisher version (URL)http://dx.doi.org/10.1016/j.tetlet.2006.06.057
Appears in Collections:(IQM) Artículos
(ICMA) Artículos
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