Coupling reaction of 4-cyclopentene-1,3-diol monoacetate and lithium alkenylborates and its application to chiral synthesis of prostaglandin intermediates

Abstract Lithium alkenylborates couple with the monoacetate of 4-cyclopentene-1,3-diol under the nickel catalyst regioselectively and stereospecifically to afford trans 1,3-isomers in good yields. Moreover, an unexpectedly high level of regio-selectivity is observed with the alkenylborates possessing the prostaglandin (PG) ω-chain structure. The present reaction is successfully applied to the asymmetric synthesis of PG intermediates 9, 15, 16 .