The first asymmetric aminolysis of trans-aromatic epoxides with anilines is described. The process affords enantioenriched anti-â-amino alcohols in up to 99% ee. The complete regio- and diastereoselectivity observed uses commercially available [Cr(Salen)Cl] as a Lewis acid catalyst and in combination with a very simple experimental procedure renders the present reaction a facile and practical tool for the synthesis of chiral nonracemic anti-â-amino alcohols.
G. Bartoli, M. Bosco, A. Carlone, M. Locatelli, M. Massaccesi, P. Melchiorre, et al. (2004). Asymmetric Aminolysis of Aromatic Epoxides: A Facile Catalytic Enantioselective Synthesis of anti-b-Amino Alcohols. ORGANIC LETTERS, 6, 2173-2176 [10.1021/ol049372t].
Asymmetric Aminolysis of Aromatic Epoxides: A Facile Catalytic Enantioselective Synthesis of anti-b-Amino Alcohols
BARTOLI, GIUSEPPE;BOSCO, MARCELLA;CARLONE, ARMANDO;LOCATELLI, MANUELA;MASSACCESI, MASSIMO;MELCHIORRE, PAOLO;SAMBRI, LETIZIA
2004
Abstract
The first asymmetric aminolysis of trans-aromatic epoxides with anilines is described. The process affords enantioenriched anti-â-amino alcohols in up to 99% ee. The complete regio- and diastereoselectivity observed uses commercially available [Cr(Salen)Cl] as a Lewis acid catalyst and in combination with a very simple experimental procedure renders the present reaction a facile and practical tool for the synthesis of chiral nonracemic anti-â-amino alcohols.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
