Asymmetric synthesis of 1H-pyrrol-3(2H)-ones from 2,3-diketoesters by combination of aldol condensation with benzilic acid rearrangement-Reference-Cited by-同舟云学术

Asymmetric synthesis of 1H-pyrrol-3(2H)-ones from 2,3-diketoesters by combination of aldol condensation with benzilic acid rearrangement

Published:2016 Issue:1 Volume:52 Page:108-111
ISSN:1359-7345
Container-title:Chemical Communications
language:en
Short-container-title:Chem. Commun.

Author:

Sha Qiang¹²³⁴⁵,Arman Hadi⁶⁷⁸⁹,Doyle Michael P.⁶⁷⁸⁹

Affiliation:

1. School of Chemical Engineering

2. Nanjing University of Science and Technology

3. Xiao Ling Wei 200

4. Nanjing 210094

5. P. R. China

6. Department of Chemistry

7. The University of Texas at San Antonio

8. San Antonio

9. USA

Abstract

A highly efficient two-step asymmetric synthesis of 1H-pyrrol-3(2H)-one derivatives from conveniently accessed 2,3-diketoesters. Aldol products are obtained with up to 89/11 d.r. and 99% ee. Benzilic acid rearrangement produces 1H-pyrrol-3(2H)-ones in good yields without loss of enantioselectivity.

Funder

National Institutes of Health

China Scholarship Council

Division of Chemistry

Publisher

Royal Society of Chemistry (RSC)

Subject

Materials Chemistry,Metals and Alloys,Surfaces, Coatings and Films,General Chemistry,Ceramics and Composites,Electronic, Optical and Magnetic Materials,Catalysis

Link

http://pubs.rsc.org/en/content/articlepdf/2016/CC/C5CC07780J

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