Diastereoselective reduction of α-aminoketones: Synthesis of anti- and syn-β-aminoalcohols-Reference-Cited by-同舟云学术

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

Published:2004-02-01 Issue:2 Volume:82 Page:87-101
ISSN:0008-4042
Container-title:Canadian Journal of Chemistry
language:en
Short-container-title:Can. J. Chem.

Author:

Fraser David S,Park Sheldon B,Chong J Michael

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.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

Link

http://www.nrcresearchpress.com/doi/pdf/10.1139/v03-165

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4. Applications of Optically Active Aryl Cyanohydrins in the Synthesis of α-Hydroxy Aldehydes, α-Hydroxy Ketones and β-Hydroxy Amines

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