Organic Chemistry Portal

Abstracts

Search:

1-Phosphino-2-sulfenylferrocenes as Planar Chiral Ligands in Enantioselective Palladium-Catalyzed Allylic Substitutions

Olga García Mancheño, Julián Priego, Silvia Cabrera, Ramón Gómez Arrayás, Tomás Llamas and Juan Carlos Carretero*

*Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco 28049 Madrid, Spain, Email: juancarlos.carreterouam.es

O. G. Mancheno, J. Priego, S. Cabrera, R. G. Arrayas, T. Llamas, J. C. Carretero, J. Org. Chem., 2003, 68, 3679-3686.

DOI: 10.1021/jo0340657 (free Supporting Information)


Abstract

The synthesis and properties of different planar chiral 1-phosphino-2-sulfenylferrocene ligands are reported. Very high enantioselectivities were obtained in the palladium-catalyzed allylic substitution of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate and nitrogen nucleophiles using readily available tert-butylsulfenyl derivatives.

see article for more reactions



Key Words

Tsuji-Trost Reaction, Allylation, Benzylations, Allylamines, Active Methylenes


ID: J42-Y2003-250