Stereofacial Assembly of Engineered Multichiral Aziridines via B/Si Ylide Insertion

Identifier:  imarina:9469311

Handle: https://hdl.handle.net/20.500.11797/imarina9469311

Authors:  Pujol, M; Tarifa, L; Tarasewicz, A; Mendez, M; Fernandez, E

Abstract:
Halo-borylsilylcarbanion reagents can be added, with complete stereofacial control, to chiral N-tert-butanesulfinyl imines, featuring an asymmetric C-C bond, followed by concomitant intramolecular asymmetric C-N bond formation. There is exclusive access to alpha,alpha-B,Si-disubstituted aziridine units containing up to four contiguous stereocenters in a single operation. In addition, complete stereochemical discrimination has been observed in N-tert-butanesulfinyl alkyl aldimines. Post-transformation of B,Si-disubstituted aziridine generates multichiral aziridine scaffolds.