Issue 13, 2022

The N-heterocyclic carbene-catalyzed [3 + 2] annulation of isoindigos with enals: the enantioselective construction of three contiguous stereogenic centers

Abstract

Constructing contiguous all-carbon quaternary stereogenic centers has posed a long-standing synthetic challenge in organic chemistry. In this work, the NHC-catalyzed enantioselective [3 + 2] annulation of enals with isoindigo was introduced as an efficient strategy for the construction of dimeric spirocyclic bisindoline alkaloid derivatives with moderate yields and good enantioselectivities. Remarkably, three contiguous stereogenic centers—including two congested all-carbon quaternary stereogenic centers—were successfully constructed in a simple one-step operation.

Graphical abstract: The N-heterocyclic carbene-catalyzed [3 + 2] annulation of isoindigos with enals: the enantioselective construction of three contiguous stereogenic centers

Supplementary files

Article information

Article type
Research Article
Submitted
07 Oct 2021
Accepted
26 Mar 2022
First published
30 Mar 2022

Org. Chem. Front., 2022,9, 3552-3557

The N-heterocyclic carbene-catalyzed [3 + 2] annulation of isoindigos with enals: the enantioselective construction of three contiguous stereogenic centers

B. Liu, J. Qi, Y. Wu, J. Li, Y. Li and X. Duan, Org. Chem. Front., 2022, 9, 3552 DOI: 10.1039/D1QO01507A

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