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Title

Diastereo‐ and Enantioselective Synthesis of Tetracyclic Cycloheptanols through (4 3) Annulation via C−C/C−H Activation Cascade.

Authors

Yan, Xin; Liu, Min; Pan, Deng; Wang, Qi; Tang, Qi; Dai, Ya‐Mei; Hu, Ping; Wang, Bi‐Qin; Huang, Genping; Song, Feijie

Abstract

Transition metal‐catalyzed annulations of four‐membered rings via C−C activation are powerful tools to construct complex fused and bridged ring systems. Despite significant progress in (4+1), (4+2) and (4+4) annulations, the (4+3) annulation remains unexplored. Herein, we develop an asymmetric Rh‐catalyzed intramolecular (4+3) annulation of α‐arylalkene‐tethered benzocyclobutenols for the synthesis of dihydrofuran‐annulated dibenzocycloheptanols with two discontinuous chiral carbon centers via a C−C and C−H activation cascade. The reaction features excellent diastereo‐ and enantioselectivities and 100 % atom economy, and is applicable to late‐stage modification of complex molecules.

Subjects

ANNULATION; CHIRAL centers

Publication

Angewandte Chemie, 2024, Vol 136, Issue 13, p1

ISSN

0044-8249

Publication type

Academic Journal

DOI

10.1002/ange.202317433

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