Abstract
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.
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