Desymmetrization of prochiral phosphanes using derivatives of (-)-cytisine
Artikel i vetenskaplig tidskrift, 2004

yHistorically, (-)-sparteine-sec-BuLi has been used to desym-metrize prochiral phosphanes. In this report, derivatives of an alkaloid extracted from the seeds of Laburnum anagyro-ides have been utilized to mimic (+)-sparteine, which is not readily available. In several cases, the enantioselectivities achieved with the (+)-Sparteine surrogates outperformed (-)-sparteine itself in the deprotonation of alkyl-substituted (as well as aryl-substituted) prochiral phosphane derivatives. In addition, use of these surrogates allows a new methodology for a chiral switch in phosphorus chemistry. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).

PHOSPHORUS

lithiation

asymmetric synthesis

PHOSPHINE BORANES

STRATEGY

CATALYZED ASYMMETRIC HYDROGENATION

LIGANDS

P-CHIRAL DIPHOSPHINES

enantioselectivity

ENANTIOSELECTIVE HYDROGENATION

sparteine

phosphanes

Författare

M. J. Johansson

Göteborgs universitet

Lennart Schwartz

Chalmers University of Technology

Mohamed Amedjkouh

Göteborgs universitet

Nina Kann

Chalmers, Institutionen för kemi och biovetenskap

European Journal of Organic Chemistry

1434-193X (ISSN)

9 1894-1896

Ämneskategorier

Kemi

DOI

10.1002/ejoc.200400006