Synthesis 2002(11): 1601-1606
DOI: 10.1055/s-2002-33345
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York

Substituted Pyridylamide Ligands in Microwave-Accelerated
Mo(0)-Catalysed Allylic Alkylations

Oscar Belda, Christina Moberg*
Department of Chemistry, Organic Chemistry, KTH, 100 44 Stockholm, Sweden
Fax: +46(8)7912333; e-Mail: kimo@kth.se;
Further Information

Publication History

Received 21 May 2002
Publication Date:
23 August 2002 (online)

Abstract

Novel 4- and 6-substituted bis-pyridylamides were prepared by microwave accelerated nucleophilic substitution of the 4- and 6-halo substituted derivatives of the parent ligand 1a. The ligands were used in the asymmetric allylation of cinnamyl carbonate catalysed by Mo(0) in which the 4-chloro- and 4-pyrrolidyl substituted ligand derivatives exhibited high regioselectivity (74:1 and 88:1, respectively) and enantioselectivity (96% ee), whereas 6-substituted ligands afforded no product under the same conditions. Other allylic substrates were used to explore the generality of the procedure.

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Belda, O.; Moberg, C., manuscript under preparation.