A ruthenium-catalysed oxidation of alcohols by hydrogen transfer has been coupled with organocatalysed condensations using pyrrolidine or piperidine, to give a,b-unsaturated esters and nitroalkenes. Reactions proceed with high (E)-selectivity and provide an efficient and straightforward route to a,b-unsaturated compounds.
Furan derivatives R 0060 2,5-Disubstituted Furans from 1,4-Alkynediols. -The synthesis of title compounds (III) and their use for the preparation of furans (V) is demonstrated. -(PRIDMORE, S. J.; SLATFORD, P. A.; WILLIAMS*, J. M. J.; Tetrahedron Lett. 48 (2007) 29, 5111-5114; Dep. Chem., Univ. Bath, Claverton Down, Bath BA2 7AY, UK; Eng.) -Mais 45-102
Carboxylic acid esters Q 0530 C-C Bond Formation from Alcohols and Malonate Half Esters Using Borrowing Hydrogen Methodology. -Alcohols are successfully converted into doubly homologated esters using a decarboxylative Knoevenagel reaction on the intermediate aldehyde. -(PRIDMORE, S. J.; WILLIAMS*, J. M. J.; Tetrahedron Lett. 49 (2008) 52, 7413-7415; Dep. Chem., Univ. Bath, Bath BA2 7AY, UK; Eng.) -Mais 14-086
Carboxylic acid esters P 0360Alkenes from Alcohols by Tandem Hydrogen Transfer and Condensation. -Ruthenium-catalyzed oxidation of benzylic alcohols by hydrogen transfer is coupled with organocatalyzed condensation to synthesize α,β-unsaturated esters and nitroalkenes. Crotononitrile acts as the hydrogen acceptor and pyrrolidine or piperidinium acetate can be used as co-catalyst. The reaction proceeds with complete (E)-selectivity and tolerates various functional groups. In place of the half esters, the carboxylate salts can be employed as well. -(HALL, M. I.; PRIDMORE, S.
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