Journal
ORGANIC LETTERS
Volume 22, Issue 9, Pages 3490-3494Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c00947
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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 Rh(2)Oct(4) and K2CO3. A synthesis of the antimicrobial natural product (+/-)-chelonin C is also reported using this novel methodology.
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