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Carbon-carbon bond formation by the reaction of organolithiums with α-lithiated cyclic enol ethers. Stereoselective synthesis of β- and γ-hydroxy di- and tri-substituted alkenes

✍ Scribed by Thinh Nguyen; Ei-ichi Negishi

Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
227 KB
Volume
32
Category
Article
ISSN
0040-4039

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✦ Synopsis

su?n?M?y a-Ltth~anon of dthydrofuran, benzofuran, and dlhydropyran followed by treatment with vanous organohthtums stereoselecnvely produces m gwd ytelds the conespondmg rmg-opened Q-alkenylhthtums. t e , (E)-B(or y)-hydroxy-to-alkenyl-co-hthtoalkenes, the hthtum atom of which can be readtly replaced with H, D, or C groups, such as CO2 and Me In search for novel 1,2-mrgration reactrons of organotranstron metal compounds,' we prepared Cp,ZrPh,* ('H NMR Cp singlet at 6 41 ppm) by treatment of C&ZrCl, with 2 equiv of PhLi at -7V'C and reacted it with 2-1tthobenzofuran (I) generated tn stm by treatment of bemofuran with 1 equtv of n-BuLr m EbO at 0°C for 1 h After hydrolyses the

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