Herein, we report
a Rh(II)-catalyzed reaction between 1-tosyl-1,2,3-triazoles
and halohydrins to provide 2,6-substituted 3,4-dihydro-2H-1,4-oxazines under basic conditions. The reaction is proposed to
undergo a rhodium carbenoid 1,3-insertion into O–H followed
by an annulation. The scope includes phenyl or alkenyl C4-substituted
triazoles and a range of halohydrins using catalytic Rh2Oct4 and K2CO3. A synthesis of the
antimicrobial natural product (±)-chelonin C is also reported
using this novel methodology.
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