Synfacts 2006(3): 0292-0292  
DOI: 10.1055/s-2006-931981
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Arylation of Aldehydes with Polymer-Supported Amino Alcohols

Contributor(s): Yasuhiro Uozumi, Tsutomu Kimura
D. Castellnou, M. Fontes, C. Jimeno, D. Font, L. Solà, X. Verdaguer, M. A. Pericàs*
Institute of Chemical Research of Catalonia, Tarragona and Universitat de Barcelona, Spain
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Publikationsverlauf

Publikationsdatum:
21. Februar 2006 (online)

Significance

Polymer-supported chiral β-amino alcohols 1 were prepared and used as chiral ligands in the enantioselective addition of organo­zinc reagents to aldehydes. The reaction of aliphatic and aromatic aldehydes with Et2Zn proceeded in the presence of chlorotritylated polystyrene-supported amino alcohol 1a to give the corresponding alcohols in 50-95% yields and with 71-91% ee (Eq. 1). Arylation of the aldehydes with Ph2Zn/Et2Zn in the presence of the ligands 1b,c gave the alcohols with high enantioselectivity, while the arylation with ligand 1a resulted in products with low enantioselectivity (Eq. 2).