A dearomatizing, thionium ion cyclization for the synthesis of functionalized, azaspirocyclic cyclohexadienones.
Thionium ions, generated by the addition of thiols to N-benzylglyoxamides, undergo a dearomatizing spirocyclization. The alkyl or arylsulfanyl group introduced during the thionium ion cyclization can act as a synthetic handle and a stereochemical control element during modifications of the azaspirocyclic frameworks (R(F) = CH(2)CH(2)C(8)F(17)).
Ovens
Caroline
C
School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, United Kingdom.
Martin
Nathaniel G
NG
Procter
David J
DJ
D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000737:chemistry; D053138:Cyclohexenes; D008968:Molecular Conformation; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry
D001372:Aza Compounds; D003510:Cyclohexanes; D053138:Cyclohexenes; D000644:Quaternary Ammonium Compounds; D013141:Spiro Compounds; D013438:Sulfhydryl Compounds; C507608:cyclohexadienone; C059915:thionium