Asymmetric synthesis of pyrrolidine-containing chemical scaffolds via Tsuji-Trost allylation of N-tert-butanesulfinyl imines

Dawood, Rafid S. and Georgiou, Irene and Wilkie, Ross P. and Lewis, William and Stockman, Robert A. (2017) Asymmetric synthesis of pyrrolidine-containing chemical scaffolds via Tsuji-Trost allylation of N-tert-butanesulfinyl imines. Chemistry - a European Journal, 23 (46). pp. 11153-11158. ISSN 1521-3765

[img] PDF - Repository staff only until 26 July 2018. - Requires a PDF viewer such as GSview, Xpdf or Adobe Acrobat Reader
Download (736kB)

Abstract

A simple and efficient asymmetric synthesis of novel sp3 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.

Item Type: Article
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.
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: 10.1002/chem.201702616
Depositing User: Smith, Ruth
Date Deposited: 19 Sep 2017 13:23
Last Modified: 14 Oct 2017 08:43
URI: http://eprints.nottingham.ac.uk/id/eprint/46526

Actions (Archive Staff Only)

Edit View Edit View