A One-Pot Reaction of α-Imino Rhodium Carbenoids and Halohydrins: Access to 2,6-Substituted Dihydro-2 H -1,4-oxazines

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-2 -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 ph...

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Bibliographic Details
Published in:Organic letters 2020-05, Vol.22 (9), p.3490-3494
Main Authors: Jones, Kieran D, Nutt, Michael J, Comninos, Elena, Sobolev, Alexandre N, Moggach, Stephen A, Miura, Tomoya, Murakami, Masahiro, Stewart, Scott G
Format: Article
Language:English
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Summary: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-2 -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 Oct and K CO . A synthesis of the antimicrobial natural product (±)-chelonin C is also reported using this novel methodology.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c00947