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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Short Communication

Asymmetric Synthesis of 2,3-Dihydrofurans via Squaramide Catalyzed Michael-Alkylation Reaction

Author(s): Zhi-Wei Ma*, Chuan-Chuan Wang, Xiao-Pei Chen, Bin Sun, Jing-Chao Tao and Quan-Jian Lv

Volume 19, Issue 10, 2022

Published on: 26 January, 2022

Page: [913 - 917] Pages: 5

DOI: 10.2174/1570178619666211231112237

Price: $65

Abstract

A highly stereoselective methodology was developed to construct dihydrofurans. In the presence of a bifunctional squaramide catalyst, the Michael addition/cyclization between cyclohexane- 1,3-dione and α-bromonitroalkenes occurred smoothly to provide the desired dihydrofurans with high to excellent yields (90-94%) and good to high enantioselectivities (80-94% ee). This catalytic protocol was compatible with a range of structurally distinct α-bromonitroalkenes.

Keywords: Asymmetric catalysis, dihydrofuran, michael-alkylation reaction, tertiary amine-squaramide, organocatalysis, α-bromonitroalkene.

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