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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Catalytic Asymmetric Desymmetrizing [4+2] Cycloaddition/Base-Mediated Oxidative Aromatization Sequence: De Novo
Subhankar Biswas1, Subhas Chandra Pan1
1Department of Chemistry, Indian Institute of Technology Guwahati, North Guwahati, Assam 781039, India.
Abstract:
Herein, an organocatalytic asymmetric desymmetrizing [4+2] cycloaddition/base-mediated oxidative aromatization reaction sequence has been developed between spirophthalide 2,5-cyclohexadienones and β-methyl cinnamaldehydes. The reaction proceeds through in situ chiral dienamine intermediate formation, and the densely functionalized spirocyclic isobenzofuranone-embedded chiral arenes were formed in high yields with excellent enantioselectivities. A 2-fold desymmetrization reaction was also performed, and the products were obtained in high enantioselectivities.
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