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The highly diastereoselective anti-aminohydroxylation of (E)-gamma-tri-iso-propylsilyloxy-alpha,beta-unsaturated esters, via conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide and subsequent in situ enolate oxidation with (+)-(camphorsulfonyl)oxaziridine, has been used as the key step in the asymmetric synthesis of N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine (20% yield over 7 steps), the anhydrophytosphingosine jaspine B (10% yield over 9 steps), 2-epi-jaspine B (14% yield over 9 steps), and the Prosopis alkaloid deoxoprosophylline (26% yield over 7 steps).

Original publication

DOI

10.1039/b801671b

Type

Journal article

Journal

Org Biomol Chem

Publication Date

07/05/2008

Volume

6

Pages

1665 - 1673

Keywords

Amides, Benzylamines, Lithium, Molecular Conformation, Organometallic Compounds, Oxidation-Reduction, Piperidines, Sphingosine, Stereoisomerism