Year: 2026
Type: preprint
Abstract: A CuBr-catalyzed one-pot protocol provides access to decahydroquinoxaline-based bis(propargylamines) from readily available terminal alkynes, aromatic aldehydes, and a C2symmetric chiral diamine. The three-component coupling proceeds at 120 °C within 12 h, affording the products in 58–93% yields with diastereomeric ratios of up to 99:1. The synthetic utility of the protocol is illustrated by the ZnI2-mediated conversion of a representative bis(propargylamine) (7a) into the corresponding axially chiral allene (8a) with 90% ee. This approach enables the stereoselective construction of bis(propargylamines) and demonstrates their application as precursors to axially chiral allenes.
Source: ChemRxiv
Authors: Alakonda, Mariappan Periasamy
Institution: University of Wyoming
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W7214107363