Steric Hindrance Facilitated Synthesis of Enynes and Their Intramolecular [4+ 2] Cycloaddition with Alkynes

JJ González, A Francesch, DJ Cárdenas…

Index: Gonzalez, Juan J.; Francesch, Andres; Cardenas, Diego J.; Echavarren, Antonio M. Journal of Organic Chemistry, 1998 , vol. 63, # 9 p. 2854 - 2857

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Citation Number: 26

Abstract

The palladium-catalyzed insertion of 1-alkynes into internal alkynes which are bent out of linearity by the interference with a peri or ortho substituent led to enynes regioselectively. The resulting enynes undergo a new type of intramolecular thermal cycloaddition, which can be used for the annulation of an aryl ring onto naphthalene derivatives to afford fluranthenes. The cyclization of (E)-1-(1-buten-3-ynyl)-8-ethynylnaphthalene could also be ...