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Synlett 1997; 1997(SI): 471-472
DOI: 10.1055/s-1997-6109
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Diastereo- and Enantioselective Synthesis of Ferrocenylphosphines by Twofold Asymmetric Ortho-Lithiation

Heiner Jendralla* , Erich Paulus
  • *HOECHST AG, Central Pharma Research, G 838, D-65926 Frankfurt, Germany, Telefax: (internat.) +49(0)69/331399; E-mail: jendralla@msmrd.frankfurt.hoechst-ag.d400.de
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Publication Date:
31 December 2000 (online)

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Enantioselective deprotonation of diamidoferrocene 1g with the n-BuLi/2-complex, followed by addition of Ph2PCl, provided enantiomerically pure monophosphine 1h after a single recrystallization. When s-BuLi/2-complex was employed, meso-diphosphine 1j was obtained with 92% de. Conversely, treatment of homochiral 1h with n-BuLi/2-complex furnished enantiomerically pure C 2-symmetric diphosphine 1i with 86-94% de. Rac-1h led to homochiral 1i and 1j in the ratio 1:1.

asymmetric ortho-lithiation - chiral ferrocenes - phosphines - catalysis