Asymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine.
نویسندگان
چکیده
The highly diastereoselective anti-aminohydroxylation of 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-diacetyl xestoaminol C (41% yield over 8 steps), N,O,O-triacetyl sphinganine (30% yield over 8 steps) and N,O,O-triacetyl sphingosine (30% yield over 7 steps).
منابع مشابه
Preparation of anti-Vicinal Amino Alcohols: Asymmetric Synthesis of d-erythro-Sphinganine, (+)-Spisulosine, and d-ribo-Phytosphingosine
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A novel, three-component C-C, C-N and C-O bond forming reaction is described. In the presence of 20 mol% CuO, this condensation reaction of CF3CHN2, nitriles, and aldehydes proceeds to afford CF3-substituted oxazolines in moderate to high yields with excellent diastereoselectivities. Subsequent ring-opening of oxazolines gives rise to the corresponding vicinal amino alcohols.
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عنوان ژورنال:
- Organic & biomolecular chemistry
دوره 6 9 شماره
صفحات -
تاریخ انتشار 2008