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New chiral amine ligands in the desymmetrization of prochiral phosphine boranes

Magnus J Johansson ; Lennart Schwartz ; Mohamed Amedjkouh ; Nina Kann (Institutionen för kemi och biovetenskap)
Tetrahedron: asymmetry (0957-4166). Vol. 15 (2004), 22, p. 3531-3538.
[Artikel, refereegranskad vetenskaplig]

P-chirogenic phosphine ligands can be prepared via desymmetrization of prochiral phosphine boranes using s-BuLi.(-)-sparteine complexes. One limitation of this method, however, has been that (+)-sparteine is not easily accessible. Herein, we show that derivatives of another alkaloid, (-)-cytisine, are useful surrogates for (+)-sparteine in the desymmetrization of prochiral phenyl-, cyclohexyl- and tert-butyl dimethyl phosphine boranes, yielding chiral phosphine boranes in up to 92% ee. Other chiral diamines were also tested but did not give as high enantioselectivity as the (-)-cytisine derivatives.

Nyckelord: ASYMMETRIC-SYNTHESIS, DIPHOSPHINE LIGANDS, DIAMINES, (-)-CYTISINE



Denna post skapades 2007-10-22. Senast ändrad 2013-05-03.
CPL Pubid: 55975

 

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Institutioner (Chalmers)

Institutionen för kemi (2001-2011)
Institutionen för kemi och biovetenskap (1900-2005)

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Kemi

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