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3-Alkoxy-1-alkynes 4 were hydroborated with pinacolborane (HBpin) to give 3-alkoxy-1-alkenylboronates 5. The latter gave (E)-3-alkoxyallylboronates (8: (E)-(MeO) 2 CHCH 2 (CH 2 ) n CH 2 OCH CHCH 2 Bpin, n=1-3) when they were subjected to iridium-catalyzed isomerization of the double bond. The corresponding (Z)-isomers 10 were synthesized by nickel-catalyzed...
Novel spirocyclization based on intramolecular 1, 4-addition and its asymmetric version have been developed using a combination of Lewis acid and 1, 2-diol. Treatment of five- and six-membered α, β-unsaturated cyclic ketones having a 4-oxopentyl group at the β-position with Lewis acid and ethylene glycol gave spiro[4.5]decane-2, 7-dione and spiro[5.5]undecane-2, 8-dione, respectively. The asymmetric...
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