Issue 67, 2024

A diastereoselective strategy for dihydrophenanthrene-fused spirooxindoles via [1,2]-phospha-Brook rearrangement

Abstract

A highly diastereoselective, one-pot strategy for spirooxindoles bearing dihydrophenanthrenes from readily available isatins and p-quinone methides (p-QMs) has been disclosed. Here, a sequential umpolung process via [1,2]-phospha-Brook rearrangement followed by Lewis acid-mediated intramolecular cyclization was employed to furnish the desired spiro product. This protocol provides access to potential medicinally relevant varieties of spirooxindolyl dihydrophenanthrenes in good to excellent yields and diastereoselectivity (>20 : 1).

Graphical abstract: A diastereoselective strategy for dihydrophenanthrene-fused spirooxindoles via [1,2]-phospha-Brook rearrangement

Supplementary files

Article information

Article type
Communication
Submitted
07 May 2024
Accepted
18 Jul 2024
First published
19 Jul 2024

Chem. Commun., 2024,60, 8904-8907

A diastereoselective strategy for dihydrophenanthrene-fused spirooxindoles via [1,2]-phospha-Brook rearrangement

A. Ali, H. K. Harit, C. Behera and R. P. Singh, Chem. Commun., 2024, 60, 8904 DOI: 10.1039/D4CC02215G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements