New Approach for the General Synthesis of Oxotetrahydroindoles via Intramolecular Cycloadditions of Azomethine Ylides with Tethered Alkynes

…, DR Hutchison, MJ Martinelli

Index: Nayyar, Naresh K.; Hutchison, Darrell R.; Martinelli, Michael J. Journal of Organic Chemistry, 1997 , vol. 62, # 4 p. 982 - 991

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Citation Number: 50

Abstract

A new method for the synthesis of oxotetrahydroindoles has been achieved employing an intramolecular dipolar cycloaddition approach involving mesoionic species (münchnones) with electron-deficient alkynes. The methodology is quite general and convergent as shown by the synthesis of a variety of tri-and tetrasubstituted oxotetrahydroindoles 18, 21, 24, 27, 30, and 34. LiI-based ester cleavage in the presence of an electrophilic acetylenic ketone ...

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