Highly Efficient Approach to Orthogonally Protected (2S,4R)- and (2S,4S)-4-Hydroxyornithine
Organic Letters2005Vol. 7(7), pp. 1423–1426
Citations Over TimeTop 10% of 2005 papers
Abstract
[reaction: see text] A concise stereoselective approach to both orthogonally protected (2S,4R)- and (2S,4S)-4-hydroxyornithine, key constituents of the biphenomycin- and clavalanine-type antibiotics, respectively, has been developed. The approach is based on bis(oxazoline) copper(II)-complex-catalyzed diastereoselective Henry reactions of nitromethane with the homoserine-derived aldehyde 6. The synthesis of this versatile chiral building block has been markedly improved.
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