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J Am Chem Soc. 2003 Mar 26;125(12):3430-1.

A new highly asymmetric chelation-controlled heck arylation.

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  • 1Department of Organic Pharmaceutical Chemistry, Uppsala Biomedical Centre, Uppsala University, Sweden.


This communication describes the development of a new highly asymmetric chelation-controlled Heck arylation. The methodology permits formation of 2-aryl-2-methyl cyclopentanones in good to very good two-step yields (45-78%) with excellent chiral enrichment (90-98% ee). In contrast to the well-known direct coupling to the enolate of a cyclic ketone, the Heck arylation of the corresponding N-methyl pyrrolidin enol ether requires neither a strong base nor a blocking of the alternative nonalkylated alpha-carbon. A chelated pi-intermediate is proposed to explain the excellent chiral induction.

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