TY - JOUR
T1 - A One-Pot Reaction of α-Imino Rhodium Carbenoids and Halohydrins
T2 - Access to 2,6-Substituted Dihydro-2 H-1,4-oxazines
AU - Jones, Kieran D.
AU - Nutt, Michael J.
AU - Comninos, Elena
AU - Sobolev, Alexandre N.
AU - Moggach, Stephen A.
AU - Miura, Tomoya
AU - Murakami, Masahiro
AU - Stewart, Scott G.
N1 - Publisher Copyright:
© 2020 American Chemical Society.
PY - 2020/5/1
Y1 - 2020/5/1
N2 - 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.
AB - 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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U2 - 10.1021/acs.orglett.0c00947
DO - 10.1021/acs.orglett.0c00947
M3 - Article
C2 - 32281806
AN - SCOPUS:85083293574
VL - 22
SP - 3490
EP - 3494
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 9
ER -