Diastereoselective addition of enantiopure lithium tert-butylsulfinylferrocene to imines.
(S)-tert-Butylsulfinylferrocene was submitted to ortho-metalation, and the corresponding lithium derivative was trapped by alkyl or aryl imines bearing various electron-withdrawing groups on the nitrogen atom (Ts, Dpp, Boc). New aminosulfoxides were obtained with complete diastereocontrol when Dpp or Boc groups were used. The absolute configuration (SS,SFc,S) has been determined by single-crystal X-ray analysis and chemical correlation. An unusual pseudocyclic boatlike transition state has been proposed to explain the stereochemical course of this reaction.
Grach
Guillaume
G
Laboratoire de Chimie Moléculaire et Thio-organique, UMR CNRS 6507, ENSICAEN, Université de Caen, 14050 Caen, France.
Santos
Jana Sopkova-de Oliveira
JS
Lohier
Jean-François
JF
Mojovic
Ljubica
L
Plé
Nelly
N
Turck
Alain
A
Reboul
Vincent
V
Metzner
Patrick
P
D018360:Crystallography, X-Ray; D005296:Ferrous Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
D005296:Ferrous Compounds; D007097:Imines; C517322:lithium tert-butylsulfinylferrocene; D008094:Lithium