Highly enantioselective Friedel-Crafts alkylations of pyrroles and indoles with alpha'-hydroxy enones under Cu(II)-simple bis(oxazoline) catalysis

Claudio Palomo; Mikel Oiarbide; Bharat G Kardak; Jesús M García; Anthony Linden

doi:10.1021/ja0423217

Highly enantioselective Friedel-Crafts alkylations of pyrroles and indoles with alpha'-hydroxy enones under Cu(II)-simple bis(oxazoline) catalysis

J Am Chem Soc. 2005 Mar 30;127(12):4154-5. doi: 10.1021/ja0423217.

Authors

Claudio Palomo¹, Mikel Oiarbide, Bharat G Kardak, Jesús M García, Anthony Linden

Affiliation

¹ Departamento de Química Orgánica I, Facultad de Química, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain. qoppanic@sc.ehu.es

PMID: 15783181
DOI: 10.1021/ja0423217

Abstract

Remarkably high and regular enantioselectivities are obtained in Friedel-Crafts alkylation reactions involving alpha'-hydroxy enone templates and Cu(II)-bis(oxazoline) complexes as catalysts. The simple elaboration of adducts provides a route to enantioenriched aldehydes, carboxylic acids, and ketones containing the pyrrole and indole frameworks.