Cycloaddition-rearrangement sequence of 2-amido substituted furans as a method of synthesizing hexahydroindolinones

A Padwa, MA Brodney, K Satake…

Index: Padwa, Albert; Brodney, Michael A.; Satake, Kyosuke; Straub, Christopher S. Journal of Organic Chemistry, 1999 , vol. 64, # 13 p. 4617 - 4626

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Citation Number: 68

Abstract

A convenient synthesis of various substituted hexahydroindolinones has been achieved by an intramolecular Diels-Alder cycloaddition (IMDAF) reaction of 2-amido substituted furans. The initially formed [4+ 2] cycloadduct undergoes nitrogen-assisted ring opening followed by deprotonation of the resulting zwitterion to give the rearranged ketone. The stereochemical outcome of the IMDAF cycloaddition has the sidearm of the tethered alkenyl group ...