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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Organocatalytic Asymmetric Dearomative Spirocyclization/Oxa-Michael Addition Sequence: Synthesis of Polycyclic
Ramji Meher1, Subhas Chandra Pan1
1Department of Chemistry, Indian Institute of Technology Guwahati, North Guwahati, Assam 781039, India.
Abstract:
Herein, an organocatalytic asymmetric dearomative spirocyclization/oxa-Michael addition sequence with a newly designed substrate having two naphthol motifs has been developed. The reaction proceeds through in situ chiral vinylidene ortho-quinone methide (VQM) intermediate formation, dearomative spirocyclization of naphthol, and an oxa-Michael addition reaction. The densely functionalized tetralone products were formed in high yields with high diastereo- and enantioselectivities.
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