Diastereoselective addition of enantiopure lithium tert-butylsulfinylferrocene to imines.
J Org Chem
; 71(26): 9572-9, 2006 Dec 22.
Article
en En
| MEDLINE
| ID: mdl-17168572
ABSTRACT
(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.
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Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Compuestos Ferrosos
/
Iminas
/
Litio
Idioma:
En
Revista:
J Org Chem
Año:
2006
Tipo del documento:
Article
País de afiliación:
Francia