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.

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.

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

• Journal Article Type: Article
• Acceptance Date: Jun 26, 2017
• Online Publication Date: Jul 26, 2017
• Publication Date: Aug 16, 2017
• Deposit Date: Sep 19, 2017
• Publicly Available Date: Sep 19, 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
• DOI: https://doi.org/10.1002/chem.201702616
• Keywords: asymmetric synthesis; imines; Michael addition; pyrrolidines; sulfur
• Public URL: https://nottingham-repository.worktribe.com/output/877761
• Publisher URL: http://onlinelibrary.wiley.com/doi/10.1002/chem.201702616/abstract
• 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.
• Contract Date: Sep 19, 2017