Stereoselective synthesis of chiral 3-aryl-1-alkynes from bromoallenes and heterocuprates

AM Caporusso, A Zampieri, LA Aronica…

Index: Caporusso, Anna Maria; Zampieri, Alessia; Aronica, Laura Antonella; Banti, Donatella Journal of Organic Chemistry, 2006 , vol. 71, # 5 p. 1902 - 1910

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Citation Number: 14

Abstract

The synthesis of chiral 3-aryl-1-alkynes 3 via cross-coupling of 3-alkyl-and 3, 3-dialkyl-1- bromo-1, 2-dienes 1 and arylbromocuprates (RCuBr) MgBr⊙ LiBr 2 was examined. With phenylcopper reagents and its para-substituted derivatives, as well as with 2-naphthyl cuprates, the reaction gave compounds 3 with high regioselectivity and good yields on the chemically pure product. On the contrary, when ortho-substituted phenyl reagents and 1- ...