Synthesis of conformationally constrained, orthogonally protected 3-azabicyclo[3.2.1]octane β-amino esters

被引：20
|
作者：
Kazi, Brigitta [1 ]
Kiss, Lorand [1 ]
Forro, Eniko [1 ]
Mandity, Istvan [1 ]
Fueloep, Ferenc [1 ,2 ]
机构：
[1] Univ Szeged, Inst Pharmaceut Chem, Eotvos 6, H-6720 Szeged, Hungary
[2] Univ Szeged, Hungarian Acad Sci, Stereochem Res Grp, H-6720 Szeged, Hungary
来源：
ARKIVOC | 2010年
关键词：
beta-amino acids; dihydroxylation; ring opening; ring closure; enzymatic resolution; INFLUENZA NEURAMINIDASE INHIBITORS; SATURATED HETEROCYCLES; RING ANALOGS; ACIDS; ENANTIOPURE; PEPTIDES; PROLINE; (+)-ANATOXIN-A; OLIGOMERS; CHEMISTRY;
D O I：
10.3998/ark.5550190.0011.904
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Novel azabicyclic beta-amino acid derivatives were readily prepared from diexo or diendo norbornene beta-amino acids. The 3-azabicyclo[3.2.1]octane skeleton was obtained by NaIO4-mediated cleavage of the dihydroxylated beta-amino ester intermediates, followed by reductive amination. Lipase-catalyzed enantioselective ring opening of racemic exo-norbornene beta-lactam allowed preparation of the corresponding azabicyclic exo beta-amino acid in enantiopure form.
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页码：31 / 39
页数：9
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