Stereoselective synthesis of cyclopentene derivatives from 1, 3-dienes

RL Danheiser, C Martinez-Davila…

Index: Danheiser, Rick L.; Martinez-Davila, Carlos; Auchus, Richard J.; Kadonaga, James T. Journal of the American Chemical Society, 1981 , vol. 103, # 9 p. 2443 - 2446

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Citation Number: 47

Abstract

(7) Wittiq reaction of hydrocinnamaldehyde with allylidenetriphenylphosphorane furnished 2 and 3 in 44% yield. Separation of isomers was achieved after cyclopropanation by column chromatography on AgN03-impregnated silica gel. Pure 3 could also be obtained by reaction of the mixture with maleic anhydride to remove 2 as its Diels-Alder adduct.(8) Wittig, G.; Schdlkopf, U. Chem. Ber. 1954, 87, 1318.(9) The stereochemistry of these alcohols ...