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A One-Pot Reaction of α-Imino Rhodium Carbenoids and Halohydrins: Access to 2,6-Substituted Dihydro-2 H -1,4-oxazines.
- Source :
-
Organic letters [Org Lett] 2020 May 01; Vol. 22 (9), pp. 3490-3494. Date of Electronic Publication: 2020 Apr 13. - Publication Year :
- 2020
-
Abstract
- 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 H -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 <subscript>2</subscript> Oct <subscript>4</subscript> and K <subscript>2</subscript> CO <subscript>3</subscript> . A synthesis of the antimicrobial natural product (±)-chelonin C is also reported using this novel methodology.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 22
- Issue :
- 9
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 32281806
- Full Text :
- https://doi.org/10.1021/acs.orglett.0c00947