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Synergistic catalysis: enantioselective cyclopropanation of alkylidene benzoxazoles by Pd(ii) and secondary amine catalysis. Scope, limitations and mechanistic insight

Synergistic catalysis: enantioselective cyclopropanation of alkylidene benzoxazoles by Pd(ii) and secondary amine catalysis. Scope, limitations and mechanistic insight
Synergistic catalysis: enantioselective cyclopropanation of alkylidene benzoxazoles by Pd(ii) and secondary amine catalysis. Scope, limitations and mechanistic insight
The reaction of alkyl-benzoxazoles with enals has been reported using a synergistic approach. It consists of the activation of enals with a secondary amine catalyst and the activation of benzoxazoles with a metal Lewis acid. This approach has also been applied to the synthesis of cyclopropanes with excellent results. We demonstrated the applicability of this reaction in a cascade reaction (cyclopropanation + ring opening) that circumvents some of the limitations of the simple Michael addition between alkyl-benzoxazoles and enals. Finally, mechanistic studies have been reported to explain the stereoselectivity of the cyclopropanation reaction that renders an unusual cis conformation.
2052-4129
806-812
Meazza, Marta
c4665645-8c77-4cfd-aa02-6bcc3341c1aa
Polo, Victor
b31ab80e-35ef-4120-b82d-921ea050d051
Merino, Pedro
a42d7ef1-fc02-49f4-8837-1294b32b6b9f
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Meazza, Marta
c4665645-8c77-4cfd-aa02-6bcc3341c1aa
Polo, Victor
b31ab80e-35ef-4120-b82d-921ea050d051
Merino, Pedro
a42d7ef1-fc02-49f4-8837-1294b32b6b9f
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441

Meazza, Marta, Polo, Victor, Merino, Pedro and Rios, Ramon (2018) Synergistic catalysis: enantioselective cyclopropanation of alkylidene benzoxazoles by Pd(ii) and secondary amine catalysis. Scope, limitations and mechanistic insight. Organic Chemistry Frontiers, 2018 (5), 806-812. (doi:10.1039/C7QO00858A).

Record type: Article

Abstract

The reaction of alkyl-benzoxazoles with enals has been reported using a synergistic approach. It consists of the activation of enals with a secondary amine catalyst and the activation of benzoxazoles with a metal Lewis acid. This approach has also been applied to the synthesis of cyclopropanes with excellent results. We demonstrated the applicability of this reaction in a cascade reaction (cyclopropanation + ring opening) that circumvents some of the limitations of the simple Michael addition between alkyl-benzoxazoles and enals. Finally, mechanistic studies have been reported to explain the stereoselectivity of the cyclopropanation reaction that renders an unusual cis conformation.

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Accepted/In Press date: 16 November 2017
e-pub ahead of print date: 28 November 2017
Published date: 2018

Identifiers

Local EPrints ID: 416604
URI: http://eprints.soton.ac.uk/id/eprint/416604
ISSN: 2052-4129
PURE UUID: 88b8deb7-9202-415b-ae6c-6a531fb5e88d
ORCID for Marta Meazza: ORCID iD orcid.org/0000-0003-4382-0626
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

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Date deposited: 03 Jan 2018 17:30
Last modified: 16 Mar 2024 06:02

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Contributors

Author: Marta Meazza ORCID iD
Author: Victor Polo
Author: Pedro Merino
Author: Ramon Rios ORCID iD

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