d-Penicillamine and l-cysteine derived thiazolidine catalysts: an efficient approach to both enantiomers of secondary alcohols

Autor: Teresa M. V. D. Pinho e Melo, M. Elisa Silva Serra, Dora C. S. Costa, Nélia C.T. Tavares, Dina Murtinho
Rok vydání: 2016
Předmět:
Zdroj: Tetrahedron. 72:5923-5927
ISSN: 0040-4020
DOI: 10.1016/j.tet.2016.08.036
Popis: d -Penicillamine derived thiazolidine ligands were prepared in a two-step synthetic sequence and used in the enantioselective alkylation of a variety of aromatic aldehydes with diethylzinc at room temperature. Excellent ee , up to >99%, and nearly complete conversions were observed. Structurally analogous l -cysteine derived thiazolidine ligands were also synthesized and tested for comparative purposes, resulting in very good, albeit slightly lower selectivities, up to 89%. The combined use of these two types of thiazolidines constitutes a very interesting strategy for synthesizing both ( S ) and ( R ) enantiomers of chiral secondary alcohols, thus leading the way to a myriad of useful optically active products with opposite absolute configurations.
Databáze: OpenAIRE