Iron-catalyzed asymmetric intramolecular cyclopropanation reactions using chiral tetramethyl-1, 1′-spirobiindane-based bisoxazoline (TMSI-BOX) ligands. Issue 5 (14th January 2019)

• Record Type: Journal Article
• Authors: Gu, Haorui; Huang, Shaoying; Lin, Xufeng
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 5(2019)
• Page Start: 1154
• Page End: 1162
• Publication Date: 2019-01-14
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob03065k
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Fe complexes of TMSI-BOX based on the tetramethyl-1, 1′-spirobiindane backbone have been developed and applied in catalytic highly enantioselective intramolecular cyclopropanation reactions. Abstract : The versatile application of chiral bisoxazoline (BOX) ligands in diverse metal-catalyzed asymmetric reactions results in growing demand for novel BOX ligands containing different motifs. Herein, the successful development of a chiral spiro bisoxazoline ligand (TMSI-BOX) on the basis of the tetramethyl-1, 1′-spirobiindane motif and bisoxazoline chelating units is described. The corresponding Fe complexes of TMSI-BOX proved to be excellent catalysts in the asymmetric intramolecular cyclopropanation reaction of diazo derivatives, providing synthetically versatile [3.1.0]bicycloalkane derivatives bearing two contiguous quaternary chiral centers with high enantiomeric purity.