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.

引用

页码：31 / 39

页数：9