A multicomponent route to functionalized amides and oxazolidinones

Christopher G. McPherson; Alasdair K. Cooper; Andrius Bubliauskas; Paul Mulrainey; Craig Jamieson; Allan J. B. Watson

doi:10.1021/acs.orglett.7b03470

A multicomponent route to functionalized amides and oxazolidinones

Christopher G. McPherson, Alasdair K. Cooper, Andrius Bubliauskas, Paul Mulrainey, Craig Jamieson, Allan J. B. Watson

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

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Abstract

An organobase-mediated, multicomponent reaction of unactivated esters, epoxides, and amines is reported, furnishing functionalized amide derivatives. A wide range of substrates are tolerated under the reaction conditions, including chiral epoxides, which react with no erosion of enantiopurity. Facile modification of the method, through replacing the ester derivative with dimethyl carbonate, enables access to the corresponding oxazolidinone derivatives.

Original language	English
Number of pages	4
Journal	Organic Letters
DOIs	https://doi.org/10.1021/acs.orglett.7b03470
Publication status	Published - 1 Dec 2017

Keywords

esters
epoxides
amines

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10.1021/acs.orglett.7b03470

McPherson-etal-OL2017-A-multicomponent-route-to-functionalized-amides-and-oxazolidinonesAccepted author manuscript, 793 KB

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title = "A multicomponent route to functionalized amides and oxazolidinones",

abstract = "An organobase-mediated, multicomponent reaction of unactivated esters, epoxides, and amines is reported, furnishing functionalized amide derivatives. A wide range of substrates are tolerated under the reaction conditions, including chiral epoxides, which react with no erosion of enantiopurity. Facile modification of the method, through replacing the ester derivative with dimethyl carbonate, enables access to the corresponding oxazolidinone derivatives. ",

keywords = "esters, epoxides, amines",

author = "McPherson, \{Christopher G.\} and Cooper, \{Alasdair K.\} and Andrius Bubliauskas and Paul Mulrainey and Craig Jamieson and Watson, \{Allan J. B.\}",

note = "This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright {\textcopyright} American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.7b03470.",

year = "2017",

month = dec,

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doi = "10.1021/acs.orglett.7b03470",

language = "English",

journal = "Organic Letters",

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publisher = "American Chemical Society",

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TY - JOUR

T1 - A multicomponent route to functionalized amides and oxazolidinones

AU - McPherson, Christopher G.

AU - Cooper, Alasdair K.

AU - Bubliauskas, Andrius

AU - Mulrainey, Paul

AU - Jamieson, Craig

AU - Watson, Allan J. B.

N1 - This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.7b03470.

PY - 2017/12/1

Y1 - 2017/12/1

N2 - An organobase-mediated, multicomponent reaction of unactivated esters, epoxides, and amines is reported, furnishing functionalized amide derivatives. A wide range of substrates are tolerated under the reaction conditions, including chiral epoxides, which react with no erosion of enantiopurity. Facile modification of the method, through replacing the ester derivative with dimethyl carbonate, enables access to the corresponding oxazolidinone derivatives.

AB - An organobase-mediated, multicomponent reaction of unactivated esters, epoxides, and amines is reported, furnishing functionalized amide derivatives. A wide range of substrates are tolerated under the reaction conditions, including chiral epoxides, which react with no erosion of enantiopurity. Facile modification of the method, through replacing the ester derivative with dimethyl carbonate, enables access to the corresponding oxazolidinone derivatives.

KW - esters

KW - epoxides

KW - amines

UR - http://pubs.acs.org/journal/orlef7

U2 - 10.1021/acs.orglett.7b03470

DO - 10.1021/acs.orglett.7b03470

M3 - Letter

SN - 1523-7060

JO - Organic Letters

JF - Organic Letters

ER -

A multicomponent route to functionalized amides and oxazolidinones

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Keywords

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