Chiral Phosphoric Acid-Catalyzed Addition of Thiols to N-Acyl Imines: Access to Chiral N,S-Acetals
Gajendrasingh K. Ingle, Michael G. Mormino, Lukasz Wojtas and Jon C. Antilla*
*Department of Chemistry, University of South Florida, 4202 East Fowler Avenue, Tampa, Florida, 33620, United States, Email: jantillausf.edu
G. K. Ingle, M. G. Mormino, L. Wojtas, J. C. Antilla, Org. Lett., 2011, 13, 4762-4765.
DOI: 10.1021/ol201899c (free Supporting Information)
see article for more reactions
Enantioenriched N,S-acetals can be prepared using chiral BINOL phosphoric acids. The reaction combines electron-rich and electron-deficient aromatic N-acyl imines with broad range of aliphatic and aromatic thiols to generate products in excellent yield and enantioselectivity. The addition reaction could also be achieved with an exceptional substrate to catalyst (S/C) molar ratio.
see article for more examples