Synthesis of orthogonally protected azepane β-amino ester enantiomers

被引：36
|
作者：
Kazi, Brigitta [1 ]
Kiss, Lorand [1 ]
Forro, Eniko [1 ]
Fulop, Ferenc [1 ,2 ]
机构：
[1] Univ Szeged, Inst Pharmaceut Chem, H-6720 Szeged, Hungary
[2] Univ Szeged, Res Grp Stereochem, H-6720 Szeged, Hungary
来源：
TETRAHEDRON LETTERS | 2010年 / 51卷 / 01期
关键词：
Cyclic beta-amino acids; Azepane; Dihydroxylation; Ring closure; Enzymatic resolution; L-IDURONIC ACID; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; PEPTIDES; INHIBITORS; DESIGN; OLIGOMERS; RING; POTENT; HELIX;
D O I：
10.1016/j.tetlet.2009.10.072
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple and convenient route is presented for the preparation of regio- and stereoisomers; of novel azepane beta-amino esters, starting from bicyclic beta-lactam isomers. The synthetic procedure consists of dihydroxylation of the olefinic bond of the alicyclic amino esters, followed by NalO(4)-mediated cleavage of the diol intermediate and reductive ring closure, which furnishes novel regioisomeric 5-aminoazepane-4-carboxylate and 3-aminoazepane-4-carboxylates. This method also allows the preparation of amino esters with an azepane skeleton in enantiomerically pure form. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：82 / 85
页数：4
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