Nickel-catalysed enantioselective reaction of secondary phosphine oxides and activated vinylcyclopropanes

• Published in: Organic & biomolecular chemistry Vol. 21; no. 15; pp. 396 - 31
• Main Authors: Huang, Zhuo, Liu, Xu-Teng, Cui, Ranran, Zhang, Qing-Wei
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 12.04.2023; Royal Society of Chemistry
• Subjects: Allyl compounds; Chemical reactions; Chemical synthesis; Chemistry; Chemistry, Organic; Enantiomers; Heavy metals; Nickel; Phosphine; Phosphine oxide; Physical Sciences; Science & Technology; Transition metals; ASYMMETRIC-SYNTHESIS; LIGANDS; RINGS; ARYLATION; VINYL-CYCLOPROPANES; BORANES; 3+2 CYCLOADDITION
• ISSN: 1477-0520; 1477-0539; 1477-0539
• DOI: 10.1039/d3ob00389b

Activated vinylcyclopropanes can form zwitterionic π-allylmetal species in the presence of transition metals and are widely used in organic synthesis. A nickel-catalyzed asymmetric allylation of secondary phosphine oxides with vinylcyclopropanes was described. Tertiary phosphine oxide products could be obtained with up to 91% yield and 92% ee. A nickel-catalyzed asymmetric allylation of racemic secondary phosphine oxides with racemic vinylcyclopropanes was described. The Tertiary phosphine oxide products were obtained with up to 91% yield and 92% ee.