Hoffmann R W, Hölzer B, Knopff O
Fachbereich Chemie der Philipps-Universität Marburg, D-35032 Marburg, Germany.
Org Lett. 2001 Jun 14;3(12):1945-8. doi: 10.1021/ol0160248.
[see reaction]. The stereochemistry of electrophilic amination has been probed using the chiral Grignard reagent 5, in which the magnesium-bearing carbon atom is the sole stereogenic center. Amination with azidomethyl phenyl sulfide 1 and with O-sulfonyloxime 2 were found to proceed with full retention of configuration.