Catalyzed Nucleophilic Substitution on Cyclopropenylmethyl Esters - Reactions via a 1,2-Methano-π-allylpalladium Intermediate

Hanno Nüske; Stefan Bräse; Armin de Meijere

doi:10.1055/s-2000-7627

Synlett 2000; 2000(10): 1467-1469
DOI: 10.1055/s-2000-7627

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Catalyzed Nucleophilic Substitution on Cyclopropenylmethyl Esters - Reactions via a 1,2-Methano-π-allylpalladium Intermediate

Hanno Nüske^* , Stefan Bräse, Armin de Meijere

^*Institut für Organische Chemie, Georg-August Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany; Fax + 49 (5 51) 39 94 75; E-mail: Armin.deMeijere@chemie-uni-goettingen.de

Abstract

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Palladium-catalyzed substitutions on primary and secondary 3,3-dimethylcyclopropenylmethyl carbonates 6a-OR, readily prepared by reaction of 3,3-dimethylcyclopropenyllithium with formaldehyde and subsequent acylation with methyl or benzyl chloroformate, with dimethylmalonate enolates and bissulfonyl-stabilized carbanions occurred regioselectively to give derivatives 12-16 in good yields (43-81%). The reaction of the tertiary acetate 6c-Me gave a mixture of the regioisomeric products 17 (43%) anf 18 (27%).

palladium catalysis - allylic substitution - cyclopropenes - enynes

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