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Stereoselective synthesis of amino acid-derived β-lactams. Experimental evidence for TADDOL as a memory of chirality enhancer

AuthorsBonache de Marcos, María Ángeles ; López-Ram-de-Víu, Pilar ; Martín Martínez, María Mercedes; García-López, M. Teresa ; Cativiela, Carlos ; González-Muñiz, Rosario
KeywordsMemory of chirality
Enantioselective synthesis
Issue DateJan-2006
CitationTetrahedron 62(1): 130-138 (2006)
AbstractIn model experiments, concerning the modulation of memory of chirality during the intramolecular alkylation of N-(p-methoxy)benzyl-N-chloroacetyl-Phe-OtBu derivative to the corresponding β-lactam, TADDOL was selected from a panel of different phase-transfer catalysts as the best chiral additive (ee up to 82%). We have demonstrated here that the degree and sign of the cyclization selectivity was virtually independent on TADDOL configuration, providing experimental proof that in this reaction this additive works as a memory of chirality enhancer and not as a real catalyst. The effect of TADDOL is strongly dependent on the starting amino acid derivative, the increase of selectivity being only observed for those with aromatic side chains.
Description9 pages, 7 tables, 1 figure, 3 schemes.
Publisher version (URL)http://dx.doi.org/10.1016/j.tet.2005.09.125
Appears in Collections:(IQM) Artículos
(ICMA) Artículos
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