Strain, silyl and steric effects on the regioselectivity of palladium(0) catalyzed allyl esters reduction as alternative to the Wittig reaction

Add time:08/21/2019    Source:sciencedirect.com

1-(1-alkenyl)-(1a-g) and 1-(1-cycloalkenyl)cycloalkyl esters (acetate, tosylate, mesylate) (4a-d) underwent palladium(0) catalyzed hydrogenolysis by sodium formate or n-butylzinc chloride as hydride sources. The regioselectivity of the reduction can be monitored either by ring strain, silyl substitution of the allyl moieties or by using the steric effect of trivalent phosphorus ligands related to their cone angles θ. Alkylidenecycloalkanes (2a-g) and cycloalkylidenecycloalkanes (5a-d) have been obtained, generally in good yields, thus providing a convenient alternative to the Wittig olefination and a new access to allylsilanes.

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