Catalytic Stereospecific Construction of Aminocyclopropanes from β-Boryl Amides
Year: 2026
Type: article
Abstract: Iridium-catalyzed reduction of β-boryl amides with tetramethyldisiloxane affords iminium ions in situ. These reactive iminium ions are directly trapped by stereospecific (invertive) reaction with the boronate, delivering aminocyclopropanes (ACPs) in excellent yield, diastereoselectivity, and enantiospecificity. The reaction applies to both secondary and tertiary benzylic boronates, allylic boronates, and α-substituted boronates, giving access to many multiply substituted ACPs.
DOI: 10.1021/jacs.5c21144
Authors: Xieyang Zhang, Ling Cheng, Matthew Chapman, James P. Morken
Institution: Boston College
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Awards: CryoProbe-enabled Bruker AVANCE NEO 500 MHz NMR Spectrometer, Bruker D8 VENTURE Diffractometer, Catalytic Enantioselective Diboration Reactions, Stereoselective Allyl Coupling Reactions, Development of Catalytic Conjunctive Coupling Reactions, G6630773366, MRI: Acquisition of a CryoProbe-Enabled NMR Spectrometer for Enhanced Efficiency and Sensitivity in Chemical and Biological Research, G9000178380
OpenAlex ID: W7125483079