Lewis Acid-Catalyzed Stereoselective Chloroamidation of Bicyclo[1.1.0]butanes: Access to the 2-Oxa-4-azabicyclo[3.1.1]hept-3-ene Scaffold

Organic Letters 2026

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Authors: Yunzhi Xie, Tianlei Du, Daotong He, Qiujie Qin, J Li, J Li, J Li, J Li, Zijun Zhou
DOI: 10.1021/acs.orglett.6c02102
Cited by: 1
References: 58

Abstract

Ring-opening difunctionalization of bicyclo[1.1.0]butanes (BCBs) provides efficient access to densely substituted cyclobutanes but often suffers from poor regio- and diastereoselectivity. We report a Lewis acid-catalyzed stereoselective chloroamidation of acyl BCBs with N -chloroamides, delivering products in up to 97% isolated yield and >20:1 dr across 40 examples, with excellent functional group tolerance and gram-scale practicality. The products are readily converted into a 2-oxa-4-azabicyclo[3.1.1]hept-3-ene scaffold with a complementary heteroatom arrangement compared with prior reports.

Fields of Study & Subjects

Catalytic C–H Functionalization Methods Radical Photochemical Reactions Synthesis and Catalytic Reactions

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
26
Pages
8400–8406
Publication date
23 June 2026
Language
EN