Catalytic asymmetric [3 + 2]-cycloaddition for stereodivergent synthesis of chiral indolyl-pyrrolidines. Issue 5 (11th January 2016)

• Record Type: Journal Article
• Authors: Arai, Takayoshi; Tokumitsu, Chihiro; Miyazaki, Tomoya; Kuwano, Satoru; Awata, Atsuko
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 5(2016)
• Page Start: 1831
• Page End: 1839
• Publication Date: 2016-01-11
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c5ob02278a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The stereochemical divergent synthesis of indolyl-pyrrolidines was accomplished using an imidazoline-aminophenol (IAP)–Ni(OAc)2 complex and a bis(imidazolidine)pyridine (PyBidine)–Cu(OTf)2 complex. Abstract : The stereochemical divergent synthesis of indolyl-pyrrolidines was accomplished using an imidazoline-aminophenol (IAP)–Ni(OAc)2 complex and a bis(imidazolidine)pyridine (PyBidine)–Cu(OTf)2 complex. The former catalyzed exo ′-selective asymmetric [3 + 2] cyclization of iminoesters with indolyl nitroalkenes, and the latter catalyzed the reaction in an endo -selective manner. These catalysts are tolerant toward highly functional substrates that supply chiral indolyl-pyrrolidine hybrids.