Gutenberg Open Science: Desymmetrization of prochiral cyclobutanones via nitrogen insertion : a concise route to chiral γ-lactams

Please use this identifier to cite or link to this item: http://doi.org/10.25358/openscience-8155

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DC Field	Value	Language
dc.contributor.author	Sietmann, Jan	-
dc.contributor.author	Ong, Mike	-
dc.contributor.author	Mück-Lichtenfeld, Christian	-
dc.contributor.author	Daniliuc, Constantin G.	-
dc.contributor.author	Wahl, Johannes M.	-
dc.date.accessioned	2022-11-17T08:29:18Z	-
dc.date.available	2022-11-17T08:29:18Z	-
dc.date.issued	2021	-
dc.identifier.uri	https://openscience.ub.uni-mainz.de/handle/20.500.12030/8170	-
dc.description.abstract	Asymmetric access to γ-lactams is achieved via a cyclobutanone ring expansion using widely available (1S,2R)-1-amino-2-indanol for chiral induction. Mechanistic analysis of the key N,O-ketal rearrangement reveals a Curtin–Hammett scenario, which enables a downstream stereoinduction (up to 88:12 dr) and is corroborated by spectroscopic, crystallographic, and computational studies. In combination with an easy deprotection protocol, this operationally simple sequence allows the synthesis of a range of optically pure γ-lactams, including those bearing all-carbon quaternary stereocenters. In addition, the formal synthesis of drug molecules baclofen, brivaracetam, and pregabalin further demonstrates the synthetic utility and highlights the general applicability of the presented method.	en_GB
dc.language.iso	eng	de
dc.rights	CC BY	*
dc.rights.uri	https://creativecommons.org/licenses/by/4.0/	*
dc.subject.ddc	540 Chemie	de_DE
dc.subject.ddc	540 Chemistry and allied sciences	en_GB
dc.title	Desymmetrization of prochiral cyclobutanones via nitrogen insertion : a concise route to chiral γ-lactams	en_GB
dc.type	Zeitschriftenaufsatz	de
dc.identifier.doi	http://doi.org/10.25358/openscience-8155	-
jgu.type.dinitype	article	en_GB
jgu.type.version	Published version	de
jgu.type.resource	Text	de
jgu.organisation.department	FB 09 Chemie, Pharmazie u. Geowissensch.	de
jgu.organisation.number	7950	-
jgu.organisation.name	Johannes Gutenberg-Universität Mainz	-
jgu.rights.accessrights	openAccess	-
jgu.journal.title	Angewandte Chemie : International edition	de
jgu.journal.volume	60	de
jgu.journal.issue	17	de
jgu.pages.start	9719	de
jgu.pages.end	9723	de
jgu.publisher.year	2021	-
jgu.publisher.name	Wiley-VCH	de
jgu.publisher.place	Weinheim	de
jgu.publisher.issn	1521-3773	de
jgu.organisation.place	Mainz	-
jgu.subject.ddccode	540	de
jgu.publisher.doi	10.1002/anie.202100642	de
jgu.organisation.ror	https://ror.org/023b0x485	-
Appears in collections:	JGU-Publikationen

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