Double [3,3]-Sigmatropic Rearrangement in the Enzymatic
Dioxygenation of Benzyl Azide: Preparation of Novel Synthetically
Valuable Azido-diols
Natalia Thevenet
Victoria de la Sovera
María
Agustina Vila
Nicolás Veiga
David Gonzalez
Gustavo Seoane
Ignacio Carrera
10.1021/ol503708v.s001
https://acs.figshare.com/articles/journal_contribution/Double_3_3_Sigmatropic_Rearrangement_in_the_Enzymatic_Dioxygenation_of_Benzyl_Azide_Preparation_of_Novel_Synthetically_Valuable_Azido_diols/2208964
Enzymatic dioxygenation
of benzyl azide by toluene dioxygenase
produces the expected enantiopure <i>cis</i>-cyclohexadienediol
along with an exocyclic diene formed by a spontaneous sequence of
two [3,3] sigmatropic shifts. This novel dienediol presents high synthetic
potential for natural product synthesis. The sigmatropic rearrangements
can be reversed by protection of the diol moiety. An optimized production
protocol for either of these valuable diols is presented.
2015-02-06 00:00:00
optimized production protocol
sequence
Sigmatropic
Synthetically
sigmatropic rearrangements
dioxygenation
diol moiety
toluene dioxygenase
exocyclic diene
product synthesis
benzyl azide
Preparation
protection
Rearrangement
novel dienediol
shift
Valuable
enantiopure
Enzymatic Dioxygenation
Benzyl Azide