Ligand-controlled switch in diastereoselectivities: catalytic asymmetric construction of spirocyclic pyrrolidine-azetidine/oxe(thie)tane derivatives

• Published in: Chemical communications (Cambridge, England) Vol. 55; no. 51; pp. 7346 - 7349
• Main Authors: Deng, Hua, Jia, Renmeng, Yang, Wu-Lin, Yu, Xingxin, Deng, Wei-Ping
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 20.06.2019; Royal Society of Chemistry
• Subjects: Alkenes; Catalysis; Chemistry; Chemistry, Multidisciplinary; Coordination compounds; copper; Crystallography; Cycloaddition; cycloaddition reactions; Derivatives; diastereoselectivity; Ligands; NMR; Nuclear magnetic resonance; Physical Sciences; Science & Technology; AZOMETHINE YLIDES; HETEROCYCLES; PYRROLIDINES; OXETANES; KINETIC RESOLUTION; ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION
• ISSN: 1359-7345; 1364-548X; 1364-548X
• DOI: 10.1039/c9cc03589c

An efficient catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides with four-membered ring-containing exocyclic alkenes has been developed, and either the exo or endo spirocyclic pyrrolidine-azetidine/oxe(thie)tane derivatives were diastereodivergently generated by employing Cu( i )/ t Bu-Phosferrox and a Cu( i )/N,O-ligand complex, respectively. Notably, various heteroatom-containing (N, O, S) exocyclic alkenes were found to be well-tolerated in this transformation. An asymmetric [3+2] cycloaddition of azomethine ylides with four-membered ring-containing dipolarophiles was developed, and either exo or endo spirocyclic pyrrolidine-azetidine/oxe(thie)tanes were obtained.