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Catalytic asymmetric one-pot synthesis of α-methylene-γ-lactams

Catalytic asymmetric one-pot synthesis of α-methylene-γ-lactams
Catalytic asymmetric one-pot synthesis of α-methylene-γ-lactams
An organocatalytic enantioselective synthesis of α-methylene-γ-lactams has been developed. The reaction between protected 2-aminomalonates and Moritae-Baylise-Hillman carbonates is catalyzed by chiral Lewis bases to afford the corresponding lactams in excellent yields and moderate to good enantioselectivities, after work-up.
0040-4020
75-82
Companyó, Xavier
446791db-6e0a-40f9-9f20-3a8e8af9803c
Geant, Pierre-Yves
f7140578-643f-4322-b905-ebe43d179866
Mazzanti, Andrea
1e31a7a1-e163-4bd4-9e72-42bc64f60277
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Companyó, Xavier
446791db-6e0a-40f9-9f20-3a8e8af9803c
Geant, Pierre-Yves
f7140578-643f-4322-b905-ebe43d179866
Mazzanti, Andrea
1e31a7a1-e163-4bd4-9e72-42bc64f60277
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441

Companyó, Xavier, Geant, Pierre-Yves, Mazzanti, Andrea, Moyano, Albert and Rios, Ramon (2014) Catalytic asymmetric one-pot synthesis of α-methylene-γ-lactams. Tetrahedron, 70 (1), 75-82. (doi:10.1016/j.tet.2013.11.028).

Record type: Article

Abstract

An organocatalytic enantioselective synthesis of α-methylene-γ-lactams has been developed. The reaction between protected 2-aminomalonates and Moritae-Baylise-Hillman carbonates is catalyzed by chiral Lewis bases to afford the corresponding lactams in excellent yields and moderate to good enantioselectivities, after work-up.

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More information

Published date: 7 January 2014
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow, Chemistry, Faculty of Natural and Environmental Sciences
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Identifiers

Local EPrints ID: 361462
URI: http://eprints.soton.ac.uk/id/eprint/361462
DOI: doi:10.1016/j.tet.2013.11.028
ISSN: 0040-4020
PURE UUID: 2f6bed9e-0e52-4421-a5c5-16caa623ae1d
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 23 Jan 2014 14:18
Last modified: 14 Mar 2024 15:51

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Contributors

Author: Xavier Companyó
Author: Pierre-Yves Geant
Author: Andrea Mazzanti
Author: Albert Moyano
Author: Ramon Rios ORCID iD

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