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

Kieran D. Jones; Michael J. Nutt; Elena Comninos; Alexandre N. Sobolev; Stephen A. Moggach; Tomoya Miura; Masahiro Murakami; Scott G. Stewart

doi:10.1021/acs.orglett.0c00947

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

Kieran D. Jones, Michael J. Nutt, Elena Comninos, Alexandre N. Sobolev, Stephen A. Moggach, Tomoya Miura, Masahiro Murakami, Scott G. Stewart

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

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-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.

Original language	English
Pages (from-to)	3490-3494
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	9
DOIs	https://doi.org/10.1021/acs.orglett.0c00947
Publication status	Published - 1 May 2020

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

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-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.",

author = "Jones, {Kieran D.} and Nutt, {Michael J.} and Elena Comninos and Sobolev, {Alexandre N.} and Moggach, {Stephen A.} and Tomoya Miura and Masahiro Murakami and Stewart, {Scott G.}",

year = "2020",

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doi = "10.1021/acs.orglett.0c00947",

language = "English",

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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.

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

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VL - 22

SP - 3490

EP - 3494

JO - Organic Letters

JF - Organic Letters

SN - 1523-7052

IS - 9

ER -

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

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