American Chemical Society
ol4c00781_si_001.pdf (15.28 MB)

Organocatalytic Asymmetric Dearomative Spirocyclization/Oxa-Michael Addition Sequence: Synthesis of Polycyclic Tetralones

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journal contribution
posted on 2024-04-03, 13:38 authored by Ramji Meher, Subhas Chandra Pan
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.