Asymmetric Cascade Michael-Cyclopropanation-Rearrangement to Spiro[Furo[2,3-d]Pyrimidines]
Manju Devi1, Najmuddin Ansari1, Ravi P Singh1
1Department of Chemistry Indian Institute of Technology Delhi, Hauz Khas, New Delhi, 110016, India.
Abstract:
An unprecedented organocatalytic enantioselective methodology has been unlocked to access oxindole-fused spiro[furo[2,3-d]pyrimidines] with high bond efficiency (two new C─C bonds and one C─O bond) and two contiguous stereocenters via Cascade Michael-Cyclopropanation-Rearrangement. A series of spiro[furo[2,3-d]pyrimidines] has been synthesized in excellent yield (up to 90%) and stereoselectivity (dr up to 99:1, er up to 97:3) from 3-chlorooxindoles and 5-alkylidene barbituric acids at room temperature. 1H NMR and HRMS studies have been conducted to define the reaction pathway.
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