Diastereo- and enantioselective synthesis of ferrocenylphosphines by twofold asymmetric ortho-lithiation

Synlett

Volumn , Issue SPEC. ISS., 1997, Pages 471-472

  Jendralla, Heiner ^a   Paulus, Erich ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002949542     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-6109     Document Type: Article

References (27)

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15. ret: (+)-1h 6.21 min , (-)-ent-1h 4.60 min.
16. 2PCl (3.0 equiv), without any effect on asymmetric induction or chemical yield.
17. A correct elemental analysis was obtained.
18. 2O provided additional 0.45 g. Combined yield: 2.35 g (85%) of 90% purity.
19. Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre. Copies of the data can be obtained on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax int. +(1223) 336-033; e-mail: teched@chemcrys. cam.ac.uk).
20. Sheldrick, G.M. SHELXTL-PLUS, an Integrated System for Solving, Refining and Displaying Crystal Structures from Diffraction Data, University of Göttingen 1990.
21. A similar effect has been reported for the di-ortho-lithiation of a 1,1′-bis(oxazolinyl)ferrocene with t-BuLi: Park, J.; Lee, S.; Ahn, K.H.; Cho, C.-W. Tetrahedron Lett. 1995, 36, 7263-7266.
22. 4): 1i δ = -22.00 ; 1j δ = -22.38.
23. Diminished yield due to increased oxygen sensitivity of crude, dissolved 1i as compared to 1h and 1j.
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