Redox-photosensitised reactions. Part 6. Stereospecific ring cleavage of 1-phenoxy-1,2,2a,3,4,8b-hexahydrocyclobuta[a]naphthalene-8b-carbonitrile and its 2-methyl derivatives by redox-photosensitisation

The highly enantioselective conjugate addition of enamides and enecarbamates to in situ-generated ortho-quinone methides, upon subsequent N,O-acetalization, gives rise to acetamido-substituted tetrahydroxanthenes with generally excellent enantio- and diastereoselectivities. A chiral BINOL-based phosphoric acid catalyst controls the enantioselectivity of the carbon-carbon bond-forming event. The products are readily converted into other xanthene-based heterocycles.

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Brønsted Acid‐Catalyzed, Highly Enantioselective Addition of Enamides to In Situ‐Generated ortho‐Quinone Methides: A Domino Approach to Complex Acetamidotetrahydroxanthenes

Saha

Schneider

2014

Chemistry A European J

151

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ChemInform Abstract: REDOX‐PHOTOSENSITIZED REACTIONS. PART 6. STEREOSPECIFIC RING CLEAVAGE OF 1‐PHENOXY‐1,2,2A,3,4,8B‐HEXAHYDROCYCLOBUTA(A)NAPHTHALENE‐8B‐CARBONITRILE AND ITS 2‐METHYL DERIVATIVES BY REDOX‐PHOTOSENSITIZATION

Majima¹,

Pac²,

Sakurai³

1981

Chemischer Informationsdienst

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Highly selective isomerization of N-allylamides catalyzed by ruthenium and rhodium complexes

Krompiec

Pigulla

Krompiec

et al. 2005

Journal of Molecular Catalysis A: Chemical

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Redox-photosensitised reactions. Part 6. Stereospecific ring cleavage of 1-phenoxy-1,2,2a,3,4,8b-hexahydrocyclobuta[a]naphthalene-8b-carbonitrile and its 2-methyl derivatives by redox-photosensitisation

Abstract: Redox-photosensitisedReactions. Bart 6.' Stereospecific RingCleavage of I -Phenoxy-l,2,2a,3,4,8b-hexa hydrocyclobuta [a] naphthalene-8b-carbonitrile and its 2-Methyl Derivatives by Redox-photosensitisation

Cited by 11 publications

References 1 publication

Brønsted Acid‐Catalyzed, Highly Enantioselective Addition of Enamides to In Situ‐Generated ortho‐Quinone Methides: A Domino Approach to Complex Acetamidotetrahydroxanthenes

Brønsted Acid‐Catalyzed, Highly Enantioselective Addition of Enamides to In Situ‐Generated ortho‐Quinone Methides: A Domino Approach to Complex Acetamidotetrahydroxanthenes

ChemInform Abstract: REDOX‐PHOTOSENSITIZED REACTIONS. PART 6. STEREOSPECIFIC RING CLEAVAGE OF 1‐PHENOXY‐1,2,2A,3,4,8B‐HEXAHYDROCYCLOBUTA(A)NAPHTHALENE‐8B‐CARBONITRILE AND ITS 2‐METHYL DERIVATIVES BY REDOX‐PHOTOSENSITIZATION

Highly selective isomerization of N-allylamides catalyzed by ruthenium and rhodium complexes

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