Issue 46, 2024

Asymmetric [3 + 3] cycloaddition of cinnamaldehyde-derived N-aryl nitrones with 2-indolemethanols enabled by chiral phosphoric acid

Abstract

We described a chiral phosphoric acid (CPA) catalyzed asymmetric [3 + 3] cycloaddition of cinnamaldehyde-derived N-aryl nitrones with 2-indolylmethanols to prepare various indole-fused 1,2-oxazines in high yields (up to 96%) with excellent enantioselectivity (>99% ee). Control experiments indicate that hydrogen bonding plays important roles in controlling the enantioselectivity of products. This strategy provides an efficient pathway to construct enantioenriched indole-fused 1,2-oxazines from N-aryl nitrones with 2-indolylmethanols.

Graphical abstract: Asymmetric [3 + 3] cycloaddition of cinnamaldehyde-derived N-aryl nitrones with 2-indolemethanols enabled by chiral phosphoric acid

Supplementary files

Article information

Article type
Communication
Submitted
18 Aug 2024
Accepted
12 Oct 2024
First published
14 Oct 2024

Org. Biomol. Chem., 2024,22, 9047-9052

Asymmetric [3 + 3] cycloaddition of cinnamaldehyde-derived N-aryl nitrones with 2-indolemethanols enabled by chiral phosphoric acid

N. Zou, Y. Wu, Z. Shang, Y. Cao, L. Liao, C. Wei, D. Mo and W. Zhou, Org. Biomol. Chem., 2024, 22, 9047 DOI: 10.1039/D4OB01365D

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