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J Org Chem. 2002 Nov 15;67(23):8197-202.

Dendritic oxazoline ligands in enantioselective palladium-catalyzed allylic alkylations.

Author information

1
Department of Fiber and Polymer Technology and Department of Chemistry, Organic Chemistry, Royal Institute of Technology, SE-100 44 Stockholm, Sweden.

Abstract

First to fourth generation dendritic substituents based on 2,2-bis(hydroxymethyl)propionic acid and (1R,2S,5R)-menthoxyacetic acid were attached to 2-(hydroxymethyl)pyridinooxazoline and bis[4-(hydroxymethyl)oxazoline] compounds. The new ligands obtained were assessed in palladium-catalyzed allylic alkylations. The first type of ligands exhibited enantioselectivity similar to that of a benzoyl ester derivative, whereas the latter type of ligands afforded products with higher selectivity than the analogous benzoyl ester. The activity of the dendritic catalysts decreased with increasing generation.

PMID:
12423151
DOI:
10.1021/jo0200116

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