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Asymmetric Synthesis of Pyrrolidine-Containing Chemical Scaffolds via Tsuji–Trost Allylation of N-tert-Butanesulfinyl Imines

Dawood, Rafid S.; Georgiou, Irene; Wilkie, Ross P.; Lewis, William; Stockman, Robert A.

Authors

Rafid S. Dawood

Irene Georgiou

Ross P. Wilkie

William Lewis

Robert A. Stockman



Abstract

© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim A simple and efficient asymmetric synthesis of novel sp 3 -rich pyrrolidine chemical scaffolds over five steps starting from simple ketones is described. Key steps involve the use of tert-butanesulfinamide as a chiral auxiliary to perform an asymmetric Tsuji–Trost allylation, with subsequent cross-metathesis with an acrylate ester and reduction of the sulfinimine/cyclisation of the resulting amine giving the pyrrolidine scaffolds in high yields and diastereoselectivites. By removing the chiral auxiliary and functionalising the ester group, the resulting scaffold core can be further derivatised.

Journal Article Type Article
Publication Date Aug 16, 2017
Journal Chemistry - A European Journal
Print ISSN 0947-6539
Electronic ISSN 1521-3765
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 23
Issue 46
Pages 11153-11158
APA6 Citation Dawood, R. S., Georgiou, I., Wilkie, R. P., Lewis, W., & Stockman, R. A. (2017). Asymmetric Synthesis of Pyrrolidine-Containing Chemical Scaffolds via Tsuji–Trost Allylation of N-tert-Butanesulfinyl Imines. Chemistry - A European Journal, 23(46), 11153-11158. https://doi.org/10.1002/chem.201702616
DOI https://doi.org/10.1002/chem.201702616
Publisher URL http://onlinelibrary.wiley.com/doi/10.1002/chem.201702616/abstract
Copyright Statement Copyright information regarding this work can be found at the following address: http://eprints.nottingh.../end_user_agreement.pdf
Additional Information This is the peer reviewed version of the following article: R. S. Dawood, I. Georgiou, R. P. Wilkie, W. Lewis, R. A. Stockman, Chemistry A European Journal 2017, 23, 11153., which has been published in final form at http://dx.doi.org/10.1002/chem.201702616 This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.

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Copyright Statement
Copyright information regarding this work can be found at the following address: http://eprints.nottingham.ac.uk/end_user_agreement.pdf





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