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Synlett 2001; 2001(9): 1464-1466
DOI: 10.1055/s-2001-16773
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Zinc Borohydride Reduction of α-Amino Ketones: A Highly Diastereoselective Synthetic Route to anti-γ-Hydroxy-β-amino Alcohols

Saumitra Sengupta* , Debasis Das, Somnath Mondal
  • *Department of Chemistry, Jadavpur University, Calcutta 700 032, India; Fax 91-033-4 73 42 66; E-mail: jusaumitra@yahoo.co.uk
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Publication Date:
28 August 2001 (online)

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A highly diastereoselective synthesis of anti-γ-hydroxy-β-amino alcohols via Zn(BH4)2 reductions of serine derived α-amino ketones is described. The latter were prepared from a serine derived γ-amino-β-ketosulfone via a α-alkylation-desulfonation sequence.

γ-hydroxy-β-amino alcohols - zinc borohydride - sphinganine - β-hydroxy leucinol - (+)-ephedrine

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