Download PDF
Synthesis 2012(7): 1057-1062  
DOI: 10.1055/s-0031-1289727
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Convenient One-Step Synthesis of Stable β-Amino Alcohol N-Boranes from α-Amino Acids

Afroditi Pinakaa,b, Georgios C. Vougioukalakis*a,c, Dimitra Dimotikalib, Vassilis Psyharisd, Kyriakos Papadopoulos*a
a Institute of Physical Chemistry, NCSR Demokritos, 15310 Athens, Greece
Fax: +30(210)6511766; e-Mail: kyriakos@chem.demokritos.gr;
b Department of Chemical Engineering, NTU Athens, 15780 Athens, Greece
c Laboratory of Organic Chemistry, Department of Chemistry, University of Athens, Panepistimiopolis Zografou, Athens 15771, Greece
Fax: +30(210)6511766; e-Mail: vougiouk@chem.uoa.gr;
d Institute of Materials Science, NCSR Demokritos, 15310 Athens, Greece
Further Information

Publication History

Received 23 January 2012
Publication Date:
27 February 2012 (online)

    Permissions and Reprints All articles of this category

Abstract

Novel, non-cyclic β-amino alcohol N-boranes are isolated from the sodium borohydride-sulfuric acid assisted direct reduction of a series of α-amino acids. The reduction takes place in one step under mild conditions and affords the products in good yields.

Key words

amino acids - β-amino alcohols - reduction - sodium borohydride - β-amino alcohol N-boranes

    References

  • 1 White SS. Kelly HC. J. Am. Chem. Soc.  1968,  90:  2009 
    Google Scholar
  • 2 Itsuno S. Wakasugi T. Ito K. Hirao A. Nakahama S. Bull. Chem. Soc. Jpn.  1985,  58:  1669 
    Google Scholar
  • 3 Leontjev AE. Vasiljeva LL. Pivnitsky KK. Russ. Chem. Bull., Int. Ed.  2004,  53:  703 
    Google Scholar
  • 4a Salunkhe AM. Burkhardt ER. Tetrahedron Lett.  1997,  38:  1523 
    Google Scholar
  • 4b Huang K. Merced FG. Ortiz-Marciales M. Meléndez HJ. Correa W. De Jesús M.
    J. Org. Chem.  2008,  73:  4017 
    Google Scholar
  • 5 Uyeda C. Biscoe M. LePlae P. Breslow R. Tetrahedron Lett.  2006,  47:  127 
    Google Scholar
  • 6 Graham T. W. Tsang C.-W. Chen X. Guo R. Jia W. Lu S.-M. Sui-Seng C. Ewart C. B. Lough A. Amoroso D. Abdur-Rashid K. Angew. Chem. Int. Ed.  2010,  49:  8708 
    Google Scholar
  • 7 Blaquiere N. Diallo-Garcia S. Gorelsky SI. Black DA. Fagnou K. J. Am. Chem. Soc.  2008,  130:  14034 
    Google Scholar
  • 8 Bowden ME. Brown IWM. Gainsford GJ. Wong H. Inorg. Chim. Acta  2008,  361:  2147 
    Google Scholar
  • 9a Scheideman M. Wang G. Vedejs E. J. Am. Chem. Soc.  2008,  130:  8669 
    Google Scholar
  • 9b Jaska CA. Temple K. Lough AJ. Manners I. J. Am. Chem. Soc.  2003,  125:  9424 
    Google Scholar
  • 10 Framer E. Vaultier M. Heteroat. Chem.  2000,  11:  218 
    Google Scholar
  • 11 Dallanegra R. Chaplin AB. Weller AS. Angew. Chem. Int. Ed.  2009,  48:  6875 
    Google Scholar
  • 12 Spielman J. Harder S. J. Am. Chem. Soc.  2009,  131:  5064 
    Google Scholar
  • 13 Mancilla T. Santiesteban F. Contreras R. Klaébé A. Tetrahedron Lett.  1982,  23:  1561 
    Google Scholar
  • 14 Tlahuext H. Santiesteban F. Garcia-Báez F. Contreras R. Tetrahedron: Asymmetry  1994,  5:  1579 
    Google Scholar
  • 15 Kelly HC. Edwards JO. Inorg. Chem.  1963,  2:  39 
    Google Scholar
  • 16 Santiesteban F. Mancilla T. Klaébé A. Contreras R. Tetrahedron Lett.  1983,  24:  759 
    Google Scholar
  • 17 Ferey V. Toupet L. Le Gall T. Mioskowski C. Angew. Chem., Int. Ed. Engl.  1996,  35:  430 
    Google Scholar
  • 18 Meyers AI. Dickman DA. Bailey TR. J. Am. Chem. Soc.  1985,  107:  7974 
    Google Scholar
  • 19 Dickman DA. Meyers AI. Smith GA. Gawley RE. Org. Synth. Coll. Vol. 7   Wiley; New York: 1990.  p.530 
    Google Scholar
  • 20 Nicolás E. Russell KC. Hruby VJ. J. Org. Chem.  1993,  58:  766 
    Google Scholar
  • 21 Giannis A. Sandhoff K. Angew. Chem., Int. Ed. Engl.  1989,  28:  218 
    Google Scholar
  • 22 Lane CF. Myatt HL. Daniels J. Hopps HB. J. Org. Chem.  1974,  39:  3052 
    Google Scholar
  • 23 Gage JR. Evans DA. Org. Synth. Coll. Vol. 8   Wiley; Chichester: 1993.  p.528 
    Google Scholar
  • 24 Demir AS. Akhmedov MI. Şeºenoglu . Turk. J. Chem.  1999,  23:  123 
    Google Scholar
  • 25 McKennon MJ. Meyers AI. Drauz K. Schwarm M.
    J. Org. Chem.  1993,  58:  3568 
    Google Scholar
  • 26 Abiko A. Masamune S. Tetrahedron Lett.  1992,  33:  5517 
    Google Scholar
  • 27 Karrer P. Portmann P. Suter M. Helv. Chim. Acta  1948,  31:  1617 
    Google Scholar
  • 28 Seki H. Koga K. Matsuo H. Ohki S. Matsuo I. Yamada S. Chem. Pharm. Bull.  1965,  13:  995 
    Google Scholar
  • 29 Delair P. Einhorn C. Einhorn J. Luche JL. J. Org. Chem.  1994,  59:  4680 
    Google Scholar
  • 30 Fehrentz JA. Califano JC. Amblard M. Loffet A. Martinez J. Tetrahedron Lett.  1994,  35:  569 
    Google Scholar
  • 31 Rodriguez M. Llinares M. Doulut S. Heitz A. Martinez J. Tetrahedron Lett.  1991,  32:  923 
    Google Scholar
  • 32 The reduction of (R,S)-N-acetyl-phenylalanine and (R,S)-N-benzoyl-alanine with three equivalents of diborane, affording the corresponding stable aminoboranes, has been reported, see: Yonemitsu O. Hamada T. Kanaoka Y. Chem. Pharm. Bull.  1969,  17:  2075 
    Google Scholar
  • 33 Poindexter GS. Meyers AI. Tetrahedron Lett.  1977,  18:  3527 
    Google Scholar
  • 34 Suhartono M. Weidlich M. Stein T. Karas M. Dürner G. Göbel MW. Eur. J. Org. Chem.  2008,  1608 
    Google Scholar
  • 35 Repke DB. Ferguson WJ. J. Heterocycl. Chem.  1976,  13:  775 
    Google Scholar
  • 36 Contreras R. Santiesteban F. Paz-Sandoval MA. Tetrahedron  1984,  40:  3829 
    Google Scholar
  • 37 Dietrich BL. Goldberg KI. Heinekey DM. Autrey T. Linehan JC. Inorg. Chem.  2008,  47:  8583 
    Google Scholar
  • 38 Aldridge S. Downs JD. Tang YC. Parson S. Clarke CM. Johnstone DLR. Robertson EH. Rankin WHD. Wann AD. J. Am. Chem. Soc.  2009,  131:  2231 
    Google Scholar
  • 39 Fanfrlik J. Lepsik M. Horinek D. Havlas Z. Hobza P. ChemPhysChem  2006,  7:  1100 
    Google Scholar
  • 40a Gribble GW. Chem. Soc. Rev.  1998,  27:  395 
    Google Scholar
  • 40b Brown HC. Subba Rao BC. J. Am. Chem. Soc.  1960,  82:  681 
    Google Scholar