Issue 15, 2019

A novel chiral DMAP–thiourea bifunctional catalyst catalyzed enantioselective Steglich and Black rearrangement reactions

Abstract

The first novel and efficient chiral DMAP–thiourea bifunctional catalyst has been successfully developed and applied in highly enantioselective acyl-transfer reactions. A series of 1,3-oxazolyl carbonates are efficiently transformed to C-carboxyazlactones (Steglich rearrangement) by employing 5 mol% of this bifunctional nucleophilic catalyst with good yields and excellent enantioselectivities (up to 90% yield and 97% ee), and 2-benzofuranylcarbonates are also converted to 3,3-disubstituted benzofuran-2-ones (Black rearrangement) with satisfactory asymmetric induction (up to 92% yield and 87% ee).

Graphical abstract: A novel chiral DMAP–thiourea bifunctional catalyst catalyzed enantioselective Steglich and Black rearrangement reactions

Supplementary files

Article information

Article type
Research Article
Submitted
22 رمضان 1440
Accepted
14 شوال 1440
First published
15 شوال 1440

Org. Chem. Front., 2019,6, 2624-2629

A novel chiral DMAP–thiourea bifunctional catalyst catalyzed enantioselective Steglich and Black rearrangement reactions

Q. Li, G. Zhang, Y. Wang, M. Mei, X. Wang, Q. Liu, X. Yang, P. Tian and G. Lin, Org. Chem. Front., 2019, 6, 2624 DOI: 10.1039/C9QO00691E

To request permission to reproduce material from this article, 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 publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements