Development of an intramolecular aryne ene reaction and application to the formal synthesis of (±)-crinine

DA Candito, D Dobrovolsky…

Index: Candito, David A.; Dobrovolsky, Dennis; Lautens, Mark Journal of the American Chemical Society, 2012 , vol. 134, # 37 p. 15572 - 15580

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Citation Number: 39

Abstract

A general and high yielding annulation strategy for the synthesis of various carbo-and heterocycles, based on an intramolecular aryne ene reaction is described. It was found that the geometry of the olefin is crucial to the success of the reaction, with exclusive migration of the trans-allylic-H taking place. Furthermore, the electronic nature of the aryne was found to be important to the success of the reaction. Deuterium labeling studies and DFT ...