Organic Letters
Letter
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oxazolidinone (R)-4p was prepared in 82% yield, which was
subsequently converted to Linezolid in three steps.12 From 1.0
g of epoxy amine (S)-2p, 0.88 g of Linezolid was prepared in
an enantiomerically pure form.
In conclusion, we have demonstrated the divergent coupling
of N-aryl epoxy amines and CO2 to prepare two different
products, cyclic carbonates and oxazolidinones. Our Al−N1O3
complex (Al-1) efficiently promoted the coupling reactions at
25−40 °C under atmospheric pressure of CO2, and the choice
of cocatalyst was crucial to control the product selectivity. In
the coupling reactions, a Lewis acid catalyst (Al-1) and a
nucleophilic cocatalyst (TBAI) provided cyclic carbonates,
whereas a Lewis acid catalyst (Al-1) and a base (DMAP)
provided oxazolidinones. Notably, stereospecific conversion
was observed in both cases, which enables us to propose
reliable mechanisms. Because chiral oxazolidinones or aminols
show biological activities, this method will enable the use of
CO2 to produce important bioactive compounds.
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ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
A. Chem. - Eur. J. 2013, 19, 6289.
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Accession Codes
tallographic data for this paper. These data can be obtained
Cambridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
6389.
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AUTHOR INFORMATION
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Corresponding Author
ORCID
(12) Mallesham, B.; Rajesh, B. M.; Reddy, P. R.; Srinivas, D.;
Trehan, S. Org. Lett. 2003, 5, 963.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
The authors are grateful for the financial support provided by
the Saudi Aramco-KAIST CO2 Management Center and the
C1 Gas Refinery Program (2016M3D3A1A01913256).
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