Synthesis of an Enantiopure Fluorous 1,2-Diphenyl-1,2-diaminoethane

Abstract

Enantiopure fluorous 1,2-diphenyl-1,2-ethanediamine bearing four fluorous ponytails and having 62.2% fluorine content has been prepared. Resolution of racemic 1,2-bis(3,5-dimethoxy­phenyl)ethane-1,2-diamine with (-)-menthyl chloroformate followed by reduction of the obtained carbamate afforded the corresponding enantiopure secondary diamines. Protection of the amino function as an aminal, followed by the cleavage of the methoxy moiety and then the introduction of the four fluorous ponytails gave after hydrolysis the enantiopure fluorous 1,2-diphenyl-1,2-ethanediamine.

Key words

enantiopure fluorous diamine - C₂ axis - resolution

References

• 1a Bennani YL. Hanessian S. Chem. Rev.  1997,  97:  3161 
• 1b Lucet D. Le Gall T. Mioskowski C. Angew. Chem. Int. Ed.  1998,  37:  2580 
• 1c Fache F. Schulz E. Tommasino M. Lemaire M. Chem. Rev.  2000,  100:  2159 
• 2 Ferrand A. Bruno M. Tommasino ML. Lemaire M. Tetrahedron: Asymmetry  2002,  13:  1379 
• 3 Li X. Chen W. Hems W. King FXJ. Tetrahedron Lett.  2004,  45:  951 
• 4 Ma Y. Liu H. Chen L. Cui X. Zhu J. Deng J. Org. Lett.  2003,  5:  2103 
• 5 Bubert C. Blacker J. Brown SM. Crosby J. Fitzjohn S. Muxworthy JP. Thorpe T. Williams JMJ. Tetrahedron Lett.  2001,  42:  4037 
• 6 Maillet C. Praveen T. Janvier P. Minguet S. Evain M. Saluzzo C. Tommasino ML. Bujoli B. J. Org. Chem.  2002,  67:  8191 
• 7 Itsuno S. Tsuji A. Takahashi M. Tetrahedron Lett.  2003,  44:  3825 
• 8 Liu PN. Gu PM. Wang F. Tu YQ. Org. Lett.  2004,  6:  169 
• 9a Maillard D. Nguefack C. Pozzi G. Quici S. Valadé B. Sinou D. Tetrahedron: Asymmetry  2000,  11:  2881 
• 9b Maillard D. Pozzi G. Quici S. Sinou D. Tetrahedron  2002,  58:  3971 
• 9c Bayardon J. Sinou D. Tetrahedron Lett.  2003,  44:  1449 
• 9d Bayardon J. Sinou D. J. Org. Chem.  2004,  69:  3121 
• 10 Corey EJ. Lee D.-H. Sarshar S. Tetrahedron: Asymmetry  1995,  6:  3 
• 11 Denmark SE. Su X. Nishigaichi Y. Coe DM. Wong K.-T. Winter SBD. Choi JY. J. Org. Chem.  1999,  64:  1958 
• 12 Maillard D. Pozzi G. Sinou D. Eur. J. Org. Chem.  2002,  269