Issue 83, 2023

Site-selective ring opening of bicyclo[n.1.0]alkanols: an Fe(ii)-catalyzed 1,6-conjugate addition to p-quinone methides

Abstract

Herein, we report an efficient synthetic strategy for an Fe(ii)-catalyzed site-selective ring opening of bicyclo[n.1.0]alkanols and their concomitant 1,6-conjugate addition to p-quinone methides. Access to tertiary carbon centers with appendaged carbocycles of distinct sizes and functional groups are achieved, under a substrate-controlled bond scission of the fused cyclopropanols. Synthetic derivatizations further enhance the utility of the protocol.

Graphical abstract: Site-selective ring opening of bicyclo[n.1.0]alkanols: an Fe(ii)-catalyzed 1,6-conjugate addition to p-quinone methides

Supplementary files

Article information

Article type
Communication
Submitted
24 Aug 2023
Accepted
22 Sep 2023
First published
25 Sep 2023

Chem. Commun., 2023,59, 12491-12494

Site-selective ring opening of bicyclo[n.1.0]alkanols: an Fe(II)-catalyzed 1,6-conjugate addition to p-quinone methides

N. Jha, S. Mondal and M. Kapur, Chem. Commun., 2023, 59, 12491 DOI: 10.1039/D3CC04135B

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