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Oxazolones in organocatalysis, new tricks for an old reagent

Oxazolones in organocatalysis, new tricks for an old reagent
Oxazolones in organocatalysis, new tricks for an old reagent
Oxazolones or azlactones are among the most-common starting materials for the synthesis of quaternary amino acids. Since the seminal works of Steglich and co-workers until the recent examples from Ooi and co-workers, azlactones have been the focus of intense research. Oxazolones are also widely used in organometallic chemistry; however, with the "renaissance" of organocatalysis, this reagent has emerged as an important starting material for a broad range of new organocatalytic asymmetric methodologies. In this Focus Review, we aim to cover all of these new organocatalytic methodologies. We begin by discussing the dynamic kinetic resolution reactions developed with azlactones. Then, we disclose the organocatalytic rearrangements. Finally, we focus on the use of oxazolones as nucleophiles in organocatalytic processes.
amino acids, asymmetric synthesis, azlactones, organocatalysis, oxazolones
1861-471X
720-734
Alba, Andrea-Nekane R.
d1750aca-a087-449c-8466-11fb54264bea
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Alba, Andrea-Nekane R.
d1750aca-a087-449c-8466-11fb54264bea
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441

Alba, Andrea-Nekane R. and Rios, Ramon (2011) Oxazolones in organocatalysis, new tricks for an old reagent. Chemistry - An Asian Journal, 6 (3), 720-734. (doi:10.1002/asia.201000636). (PMID:21344651)

Record type: Article

Abstract

Oxazolones or azlactones are among the most-common starting materials for the synthesis of quaternary amino acids. Since the seminal works of Steglich and co-workers until the recent examples from Ooi and co-workers, azlactones have been the focus of intense research. Oxazolones are also widely used in organometallic chemistry; however, with the "renaissance" of organocatalysis, this reagent has emerged as an important starting material for a broad range of new organocatalytic asymmetric methodologies. In this Focus Review, we aim to cover all of these new organocatalytic methodologies. We begin by discussing the dynamic kinetic resolution reactions developed with azlactones. Then, we disclose the organocatalytic rearrangements. Finally, we focus on the use of oxazolones as nucleophiles in organocatalytic processes.

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More information

e-pub ahead of print date: 11 January 2011
Published date: 1 March 2011
Keywords: amino acids, asymmetric synthesis, azlactones, organocatalysis, oxazolones
Organisations: Chemistry

Identifiers

Local EPrints ID: 347696
URI: https://eprints.soton.ac.uk/id/eprint/347696
ISSN: 1861-471X
PURE UUID: 29fa7e71-953a-4c80-8bd8-39bc5739117a
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 29 Jan 2013 11:15
Last modified: 06 Jun 2018 12:29

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