A One-Pot Reaction of α-Imino Rhodium Carbenoids and Halohydrins: Access to 2,6-Substituted Dihydro-2H-1,4-oxazines.
Org Lett
; 22(9): 3490-3494, 2020 05 01.
Article
em En
| MEDLINE
| ID: mdl-32281806
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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2020
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Article