ortho-Metalation of enantiopure aromatic sulfoxides and stereocontrolled addition to imines |
| |
Authors: | Le Fur Nicolas Mojovic Ljubica Plé Nelly Turck Alain Reboul Vincent Metzner Patrick |
| |
Institution: | Laboratoire de Chimie Organique Fine et Hétérocyclique, UMR CNRS 6014, IRCOF, INSA, B.P. 08, 76131 Mont Saint Aignan, France. |
| |
Abstract: | Enantiopure aromatic (phenyl, naphthyl) and heteroaromatic (pyridyl, quinolyl, diazinyl) sulfoxides have been synthesized by reaction of (S)-tert-butyl tert-butanethiosulfinate with aryl- or heteroaryllithium derivatives. The ortho-directed metalation of the sulfoxides was performed with lithium bases. Subsequent addition of the lithiated intermediates to N-tosylimines afforded tosylaminoalkyl tert-butylsulfinyl arenes. In most cases a complete asymmetric induction was highlighted in favor of (S,S) isomers. Heating the aminosulfoxides provided an original cyclization to form novel cyclic sulfenamides. A novel enantiopure synthesis of a benzylamine was described. An application of an enantiopure aminosulfoxide as N,S ligand for the asymmetric catalysis of allylic nucleophilic substitution has been successfully tested. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|