Synthesis 2012; 44(11): 1625-1627
DOI: 10.1055/s-0031-1291039
short paper
© Georg Thieme Verlag Stuttgart · New York

Simple Preparation of β-Amino Alcohols Possessing a tert-Butyl Group at the α-Carbon

James T. Zacharia
Department of Chemistry, Graduate School of Science, Kobe University, Nada, Kobe, 657-8501, Japan, Fax: +81(78)8035688   Email: mhayashi@kobe-u.ac.jp
,
Takanori Tanaka
Department of Chemistry, Graduate School of Science, Kobe University, Nada, Kobe, 657-8501, Japan, Fax: +81(78)8035688   Email: mhayashi@kobe-u.ac.jp
,
Yumiko Uesaka
Department of Chemistry, Graduate School of Science, Kobe University, Nada, Kobe, 657-8501, Japan, Fax: +81(78)8035688   Email: mhayashi@kobe-u.ac.jp
,
Masahiko Hayashi*
Department of Chemistry, Graduate School of Science, Kobe University, Nada, Kobe, 657-8501, Japan, Fax: +81(78)8035688   Email: mhayashi@kobe-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 12 March 2012

Accepted after revision: 12 April 2012

Publication Date:
08 May 2012 (online)


Abstract

Simple preparation of β-amino alcohols possessing a tert-butyl group at the α-carbon was achieved. These β-amino alcohols proved to work effectively as catalysts in the enantioselective alkylation of aldehydes.

Supporting Information

 
  • References


    • For reviews, see:
    • 1a Noyori R, Kitamura M. Angew. Chem. Int. Ed. 1991; 30: 49
    • 1b Soai K, Niwa S. Chem. Rev. 1992; 92: 833
    • 1c Pu L, Yu H.-B. Chem. Rev. 2001; 101: 757
    • 2a Superchi S, Mecca T, Giorgio E, Rosini C. Tetrahedron: Asymmetry 2001; 12: 1235
    • 2b Le GoanvicD, Holler M, Pale P. Tetrahedron: Asymmetry 2002; 13: 119
    • 2c Wolf C, Francis CJ, Hawes PA, Shah M. Tetrahedron: Asymmetry 2002; 13: 1733
    • 2d Huang HM, Zheng Z, Chen HL, Bai C, Wang J. Tetrahedron: Asymmetry 2003; 14: 1285
    • 2e Kang SW, Ko DH, Kim KH, Ha D.-C. Org. Lett. 2003; 5: 4517
    • 2f Bauer T, Gajewiak J. Tetrahedron 2004; 60: 9163
    • 2g Szakonyi Z, Balazs A, Martinek TA, Fülöp F. Tetrahedron: Asymmetry 2006; 17: 199
    • 2h Hsieh S.-S, Gau H.-M. Chirality 2006; 18: 569
    • 2i Bisai A, Singh PK, Singh VK. Tetrahedron 2007; 63: 598
    • 2j Paolucci C, Rosini G. Tetrahedron: Asymmetry 2007; 18: 2923
    • 2k Martins JE. D, Wills M. Tetrahedron: Asymmetry 2008; 19: 1250
    • 2l Pisani L, Superchi S. Tetrahedron: Asymmetry 2008; 19: 1784
    • 2m Mao J. Synth. Commun. 2009; 39: 3710
  • 3 Noyori R, Suga S, Kawai K, Okada S, Kitamura M, Oguni N, Hayashi M, Kaneko T, Matsuda Y. J. Organomet. Chem. 1990; 382: 19
    • 4a Métro T.-X, Appenzeller J, Pardo DG, Cossy J. Org. Lett. 2006; 8: 3509
    • 4b Métro T.-X, Pardo DG, Cossy J. Chem.–Eur. J. 2009; 15: 1064