Lewis Acid-Catalyzed Divergent (4+3)/(4+2) Annulations of o -Quinone Methides with Bicyclo[1.1.0]butanes Lead to sp 3 -Rich Oxabicyclic Frameworks

Organic Letters 2026 Open access

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Authors: Soumik Mondal, Manveer Patel, Subhadeep Hazra, Saumen Hajra, Jaideep Saha
DOI: 10.1021/acs.orglett.5c04897
Cited by: 5
References: 67

Abstract

Benzannulation strategies that attach a planar arene ring to cyclic, saturated, three-dimensional bridged motifs are becoming valuable for drug discovery. Herein, a Lewis acid-catalyzed [4+3] annulation of in situ -generated o -QMs with bicyclo[1.1.0]butanes is developed. Reaction modulation further leveraged a telescoped [4+2] annulation of o -QMs with the in situ -formed cyclobutanes, leading to diversified sp 3 -rich oxabicyclic architectures. Overall, this study expands the scope for a new bioisosteric space for medicinal chemistry.

Fields of Study & Subjects

Synthesis of Indole Derivatives Catalytic Alkyne Reactions Multicomponent Synthesis of Heterocycles

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
3
Pages
954–959
Publication date
9 January 2026
Language
EN