A new class of readily accessible chiral amino-phosphine precatalysts derived from 9-amino (9-deoxy) epi-cinchona alkaloids has been developed. In combination with Ag(I) salts, these amino-phosphines performed as effective cooperative Brønsted base/Lewis acid catalysts in the asymmetric aldol reaction of isocyanoacetate nucleophiles. Under optimal conditions, high diastereoselectivities (up to 98%) and enantioselectivities (up to 98%) were obtained.
A new family of cinchona-derived amino phosphine precatalysts:application to the highly enantio- and diastereoselectivesilver-catalyzed isocyanoacetate aldol reaction / Sladojevich, F.; Trabocchi, Andrea; Guarna, Antonio; Dixon, D. J.. - In: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. - ISSN 0002-7863. - STAMPA. - 133:(2011), pp. 1710-1713. [10.1021/ja110534g]
A new family of cinchona-derived amino phosphine precatalysts:application to the highly enantio- and diastereoselectivesilver-catalyzed isocyanoacetate aldol reaction
TRABOCCHI, ANDREA;GUARNA, ANTONIO;
2011
Abstract
A new class of readily accessible chiral amino-phosphine precatalysts derived from 9-amino (9-deoxy) epi-cinchona alkaloids has been developed. In combination with Ag(I) salts, these amino-phosphines performed as effective cooperative Brønsted base/Lewis acid catalysts in the asymmetric aldol reaction of isocyanoacetate nucleophiles. Under optimal conditions, high diastereoselectivities (up to 98%) and enantioselectivities (up to 98%) were obtained.
I documenti in FLORE sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
