Work

Native-carboxylate-assisted enantioselective C–H annulations with allenes and 1,3-dienes on ferrocene

Year: 2025

Type: article

Abstract: Native carboxylate as a directing group in enantioselective C-H activation results in poor stereodiscrimination, due to dynamic ligand exchange during the enantiodetermining concerted metalation-deprotonation (CMD) step. Herein, we present the synthesis of a new class of chiral ferrocene-fused isochroman derivatives from the readily available native carboxylate functionality. The Pd(II)/MPAA-derived enantioselective C-H activation and intermolecular annulation with allenes and 1,3-dienes afforded structurally diverse ferrocene-fused isochromans with up to 80% yield and 96 : 4 enantioselectivity.

Source: Chemical Communications

DOI: 10.1039/d5cc06160a

Authors: Devendra Parganiha, Yagya Dutt Upadhyay, Sumit Khevariya, Pruthviraj Amar Patil, Svastik Jaiswal, Yogesh Dhasmana, Sangit Kumar

Institution: Indian Institute of Science Education and Research, Bhopal

Language: English

Topic: Catalytic C–H Functionalization Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Funders: Department of Science and Technology, Ministry of Science and Technology, India, University Grants Committee, Science and Engineering Research Board

Awards: G6319186174, G7472118393, G8593689085, G8850288557