Diastereoselective reduction of α-aminoketones: synthesis of anti-and syn-β-aminoalcohols

DS Fraser, SB Park, JM Chong

Index: Fraser, David S.; Park, Sheldon B.; Chong, J. Michael Canadian Journal of Chemistry, 2004 , vol. 82, # 2 p. 87 - 101

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Citation Number: 19

Abstract

Reduction of Nt-BOC-protected-N-alkyl α-aminoketones with LiEt3BH or Li (s-Bu) 3BH furnishes protected syn-β-aminoalcohols with high selectivities. In contrast, removal of the BOC group followed by reduction of the aminoketone gives anti-β-aminoalcohols with variable selectivities. With aromatic ketones, selectivities are typically high while aliphatic ketones show mediocre to high selectivities depending on steric considerations. Key ...