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Synthesis of variously 2-substituted alkyl (Z)- and (E)-2-alkenoates and (Z)- and (E)-α-ylidene-γ-butyrolactones via palladium-mediated cross-coupling reactions between organostannanes and organic halides by Fabio Bellina; Adriano Carpita; Massimo De Santis; Renzo Rossi is a Chemistry article available to read on EtoBox.

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Stereoisomerieally pure trisubstituted a$-unsaturated esters of general formula 7 have been efficiently synthetized using two different protocols. The fust one involves the palladium(0)/copper(I)-mediated cross-coupling reaction between alkyl(~-2-tributylstannyI-2-alkenoates, (E)-2, and aryl or alkenyl iodides. The second protocol, which allows to prepare stexeodefd L-a@, 2-methyl, 2-(1-nlkenyl) as well as 24cyl substituted a&unsaturated esters, is based on the cross-coupling reaction between easily available alkyl Q-or (E)-2-halo-2-akenoates and organostannanes in NMP, in the presence of catalytic amounts of Pdt&(PhCN),. A&It, and CuI. @)-and (E)-2ethenyl substituted a$-unsaturated esters prepared according to this procedure have been proven to be useful precursom to (Z)-and Q-a-ylidene-~butytolactones, Q-and (&It, respectively. Trisubstitutcd o$-unsaturated esters arc an important class of compounds as synthetic intcrmediatcs of many naturally-occurring substances. Stcrcoselcctive construction of such esters is a fundamental challenge in organic synthesis1 . In the context of our studies on the synthesis and applications of 1-alkenylstatmatres bearing a functional substituent in

Who reads Synthesis of variously 2-substituted alkyl (Z)- and (E)-2-alkenoates and (Z)- and (E)-α-ylidene-γ-butyrolactones via palladium-mediated cross-coupling reactions between organostannanes and organic halides?

Author

Fabio Bellina; Adriano Carpita; Massimo De Santis; Renzo Rossi

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

1994

Language

EN

Field

Chemistry (Physical Sciences)