Please use this identifier to cite or link to this item:
http://doi.org/10.25358/openscience-8155
Authors: | Sietmann, Jan Ong, Mike Mück-Lichtenfeld, Christian Daniliuc, Constantin G. Wahl, Johannes M. |
Title: | Desymmetrization of prochiral cyclobutanones via nitrogen insertion : a concise route to chiral γ-lactams |
Online publication date: | 17-Nov-2022 |
Year of first publication: | 2021 |
Language: | english |
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. |
DDC: | 540 Chemie 540 Chemistry and allied sciences |
Institution: | Johannes Gutenberg-Universität Mainz |
Department: | FB 09 Chemie, Pharmazie u. Geowissensch. |
Place: | Mainz |
ROR: | https://ror.org/023b0x485 |
DOI: | http://doi.org/10.25358/openscience-8155 |
Version: | Published version |
Publication type: | Zeitschriftenaufsatz |
License: | CC BY |
Information on rights of use: | https://creativecommons.org/licenses/by/4.0/ |
Journal: | Angewandte Chemie : International edition 60 17 |
Pages or article number: | 9719 9723 |
Publisher: | Wiley-VCH |
Publisher place: | Weinheim |
Issue date: | 2021 |
ISSN: | 1521-3773 |
Publisher DOI: | 10.1002/anie.202100642 |
Appears in collections: | JGU-Publikationen |
Files in This Item:
File | Description | Size | Format | ||
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desymmetrization_of_prochiral-20221021130305159.pdf | 1.5 MB | Adobe PDF | View/Open |