Desymmetrization of prochiral phosphanes using derivatives of (-)-cytisine
Journal article, 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
Author
M. J. Johansson
University of Gothenburg
Lennart Schwartz
Chalmers University of Technology
Mohamed Amedjkouh
University of Gothenburg
Nina Kann
Chalmers, Department of Chemistry and Bioscience
European Journal of Organic Chemistry
1434-193X (ISSN)
9 1894-1896Subject Categories (SSIF 2011)
Chemical Sciences
DOI
10.1002/ejoc.200400006