Asymmetric synthesis of δ-amino acid derivatives via diastereoselective vinylogous Mannich reactions between N-tert-butanesulfinyl imines and dioxinone-derived lithium dienolate

Guijun Li; Xiaoliang Xu; Hongchang Tian; Xiaotong Liu; Wen Chen; Xiaodong Yang; Hongbin Zhang

doi:10.1039/C7RA10529K

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

Asymmetric synthesis of δ-amino acid derivatives via diastereoselective vinylogous Mannich reactions between N-tert-butanesulfinyl imines and dioxinone-derived lithium dienolate†

Guijun Li,^ab Xiaoliang Xu,^a Hongchang Tian,^a Xiaotong Liu,^a Wen Chen,*^a Xiaodong Yang

^a and Hongbin Zhang

*^a

Author affiliations

* Corresponding authors

^a Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan, P. R. China
E-mail: zhanghb@ynu.edu.cn, chenwenchem@163.com
Fax: +86-871-65035538
Tel: +86-871-65031119

^b College of Chemistry and Environmental Science, Qujing Normal University, Qujing, Yunnan, P. R. China

Abstract

A diastereoselective vinylogous Mannich reaction between the N-tert-butanesulfinyl imines and dioxinone-derived lithium dienolate was developed. A variety of aldimines, ketimines and isatin-derived ketimines are suitable for this process. On the basis of X-ray crystallography of products, a predictive model for this transformation was provided.

Download options Please wait...

Supplementary files

Article information

DOI: https://doi.org/10.1039/C7RA10529K
Article type: Paper
Submitted: 22 Sep 2017
Accepted: 26 Oct 2017
First published: 01 Nov 2017
This article is Open Access

Download Citation

RSC Adv., 2017,7, 50822-50828

Permissions

Request permissions

Asymmetric synthesis of δ-amino acid derivatives via diastereoselective vinylogous Mannich reactions between N-tert-butanesulfinyl imines and dioxinone-derived lithium dienolate

G. Li, X. Xu, H. Tian, X. Liu, W. Chen, X. Yang and H. Zhang, RSC Adv., 2017, 7, 50822 DOI: 10.1039/C7RA10529K

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

RSC Advances

Asymmetric synthesis of δ-amino acid derivatives via diastereoselective vinylogous Mannich reactions between N-tert-butanesulfinyl imines and dioxinone-derived lithium dienolate†

Abstract

Supplementary files

Article information

Download Citation

Permissions

Asymmetric synthesis of δ-amino acid derivatives via diastereoselective vinylogous Mannich reactions between N-tert-butanesulfinyl imines and dioxinone-derived lithium dienolate

Social activity

Search articles by author

Spotlight

Advertisements