Electron‐rich 2‐Pyridones, III: Stereochemistry and Reactivity of Phenylsulfonyl‐ substituted 2‐Azabicyclo[2.2.2]octan‐6‐ones | Zendy

Herdeis Claus | Zendy; HartkeKarger Claudia | Zendy; Lotter Hermann | Zendy

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Electron‐rich 2‐Pyridones, III: Stereochemistry and Reactivity of Phenylsulfonyl‐ substituted 2‐Azabicyclo[2.2.2]octan‐6‐ones

Author(s) -

Herdeis Claus,

HartkeKarger Claudia,

Lotter Hermann

Publication year - 1990

Publication title -

archiv der pharmazie

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.468

H-Index - 61

eISSN - 1521-4184

pISSN - 0365-6233

DOI - 10.1002/ardp.19903231112

Subject(s) - carbanion , sulfone , deprotonation , chemistry , cycloaddition , reactivity (psychology) , alkylation , conjugate , sulfonyl , medicinal chemistry , stereochemistry , organic chemistry , catalysis , ion , medicine , alkyl , mathematical analysis , alternative medicine , mathematics , pathology

[4+2]cycloaddition of electron‐rich 5‐benzyloxy‐2‐pyridone ( 1 ) with phenylvinyl sulfone furnished, after functional group transformation, 2 in a syn/anti ratio of 3/7. Deprotonation with LDA provided the thermodynamic stable 2a . The α‐sulfonyl carbanion can be alkylated to 4 . During reductive desulfonylation complete epimerisation to 5 occured. Synthesis of 5b was also accomplished by conjugate addition of ethylphenylsulfonyl carbanion to 11 .

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