Synthesis of Enantiopure Trans-N-Boc-3-Aminobicyclo[2.2.2]octane-2-carboxylic acids and Their Bicyclic 1,3-Amino alcohol Derivatives via the [4+2] Cycloaddition of 1,3-Cyclohexadiene to a Chiral β-Nitroacrylate

被引：11
|
作者：
Calmes, Monique [1 ]
Escale, Francoise [1 ]
Didierjean, Claude [2 ]
Martinez, Jean [1 ]
机构：
[1] Univ Montpellier 2, UMR 5247, IBMM, CNRS,UM1,UM2, F-34095 Montpellier 5, France
[2] CNRS, UMR 8036, UHP, Lab Cristallog & Modelisat Mat Mineraux & Biol, F-54506 Vandoeuvre Les Nancy, France
来源：
CHIRALITY | 2011年 / 23卷 / 03期
关键词：
asymmetric synthesis; Diels-Alder reactions; bicyclic beta-amino acids; bicyclic-1,3-amino alcohol; chiral beta-nitroacrylate; DIELS-ALDER REACTION; AMINO-ACIDS; ASYMMETRIC-SYNTHESIS; MEDICINAL CHEMISTRY; CARBOXYLIC-ACIDS; REDUCTION;
D O I：
10.1002/chir.20906
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
The chiral beta-nitroacrylate 2 derived from the (R)- or (S)-4-(3-hydroxy-4,4-dimethyl-2-oxopyrrolidin-1-yl) benzoic acid 1 acts as a reactive dienophile in a diastereoselective Diels-Alder reaction with 1,3-cyclohexadiene. The major cycloadducts have been isolated and transformed into enantiopure trans(2S,3S)-or (2R,3R)-N-Boc-3-aminobicyclic[2,2,2]octane-2-carboxylic acids 5. The trans-(2S,3S)-or (2R,3R)-N-Boc 3-(hydoxymethyl)-2-aminobicyclic[2,2,2] octane 6 derivatives were also obtained. Chirality 23:245-249, 2011. (C) 2010 Wiley-Liss, Inc.
引用
收藏
页码：245 / 249
页数：5
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