Diastereoselective reduction of α-aminoketones: Synthesis of anti- and syn-β-aminoalcohols
- 1 February 2004
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 82 (2) , 87-101
- https://doi.org/10.1139/v03-165
Abstract
Reduction of N-t-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 words: β-aminoalcohol, diastereoselective reduction.Keywords
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