Premium
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 .