Silver oxide mediated novel SET oxidative cyclization: stereoselective synthesis of 3-azabicyclo[.1.0]alkanes

For the first time, silver oxide catalyzed SET-oxidative cyclization of an α-amidinoester tethered with an alkene, leading to a novel cyclopropane-fused cyclic amidine, has been developed. This efficient method permits easy access to the pharmaceutically important 3-azabicyclo[ n .1.0]alkane framewo...

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Veröffentlicht in:	Chemical communications (Cambridge, England) England), 2019-07, Vol.55 (53), p.7647-765
Hauptverfasser:	Veeranna, Kirana Devarahosahalli, Das, Kanak Kanti, Baskaran, Sundarababu
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkanes Crystallography Cyclopropane Reagents Silver oxides Stereoselectivity
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container_title	Chemical communications (Cambridge, England)
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creator	Veeranna, Kirana Devarahosahalli Das, Kanak Kanti Baskaran, Sundarababu
description	For the first time, silver oxide catalyzed SET-oxidative cyclization of an α-amidinoester tethered with an alkene, leading to a novel cyclopropane-fused cyclic amidine, has been developed. This efficient method permits easy access to the pharmaceutically important 3-azabicyclo[ n .1.0]alkane framework, having a quaternary centre. The generality of SET oxidative cyclization using persulfate as a co-oxidant has been demonstrated with a wide variety of α-amidinoesters in good yields. Unusual chemoselective dialkylation of amidine with Grignard reagent and regioselective opening of the cyclopropane ring using organocopper reagent have also been developed. Stereoselective synthesis of 3-azabicyclo[ n .1.0]alkane by silver oxide catalyzed SET oxidative cyclization.
doi_str_mv	10.1039/c9cc03647d
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source	Royal Society Of Chemistry Journals; Alma/SFX Local Collection
subjects	Alkanes Crystallography Cyclopropane Reagents Silver oxides Stereoselectivity
title	Silver oxide mediated novel SET oxidative cyclization: stereoselective synthesis of 3-azabicyclo[.1.0]alkanes
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