Enantio- and Diastereoselective Nitro-Mannich Reaction of α-Aryl Nitromethanes with Amidosulfones Catalyzed by Phase-Transfer Catalysts.
J Org Chem
; 82(9): 4668-4676, 2017 05 05.
Article
em En
| MEDLINE
| ID: mdl-28418251
ABSTRACT
A high-yield, highly diastereo- and enantioselective nitro-Mannich reaction of α-aryl nitromethanes with amidosulfones catalyzed by a novel chiral phase-transfer catalyst, bearing multiple H-bonding donors, derived from quinine was developed. A variety of α-aryl nitromethanes and amidosulfones were investigated; and the corresponding products were obtained in excellent yields with excellent diastereo- and enantioselectivities (up to 99% yield, > 991 dr and >99% ee). As a demonstration of synthetic utility, the resulting ß-nitroamines could be converted to corresponding meso-symmetric and optically pure unsymmetric anti-1,2-diarylethylenediamines.
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01-internacional
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MEDLINE
Idioma:
En
Ano de publicação:
2017
Tipo de documento:
Article