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Issue 15, 2019
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A novel chiral DMAP–thiourea bifunctional catalyst catalyzed enantioselective Steglich and Black rearrangement reactions

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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

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Article information


Submitted
27 May 2019
Accepted
17 Jun 2019
First published
18 Jun 2019

Org. Chem. Front., 2019,6, 2624-2629
Article type
Research Article

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

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