Decarbonylative radical cyclization of α-amino selenoesters upon electrophilic alkenes. A general method for the 6-azabicyclo [3.2. 1] octane synthesis
J Quirante, X Vila, C Escolano… - The Journal of Organic …, 2002 - ACS Publications
J Quirante, X Vila, C Escolano, J Bonjoch
The Journal of Organic Chemistry, 2002•ACS Publications… In our approach to the 6-azabicyclo[3.2.1]octane nucleus, we chose to explore the
decarbonylative radical cyclization of α-amino selenoesters upon deactivated alkenes (Scheme
1). Acyl radicals can be generated by hydride treatment of selenoesters, and their reactions can
be classified into three types: (i) the atom or group transfer reaction on the acyl carbon, as
exemplified by hydrogen abstraction to give the corresponding aldehydes; (ii) the addition to …
We next attempted to carry out the cyclization process from the selenoester 19, since there are …
decarbonylative radical cyclization of α-amino selenoesters upon deactivated alkenes (Scheme
1). Acyl radicals can be generated by hydride treatment of selenoesters, and their reactions can
be classified into three types: (i) the atom or group transfer reaction on the acyl carbon, as
exemplified by hydrogen abstraction to give the corresponding aldehydes; (ii) the addition to …
We next attempted to carry out the cyclization process from the selenoester 19, since there are …
α-Amino selenoester-tethered electronically poor alkenes on treatment with tributyltin hydride or TTMSS undergo intramolecular radical cyclization to provide 6-azabicyclo[3.2.1]octanes through 1-aminomethyl radical intermediates.
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