Stereoselective divergent synthesis of 1,2-aminoalcohol-containing heterocycles from a common chiral nonracemic building block

被引：3
作者：
Geant, Pierre-Yves [1 ]
Grenet, Erwann [1 ]
Martinez, Jean [1 ]
Salom-Roig, Xavier J. [1 ]
机构：
[1] Univ Montpellier, IBMM, UMR 5247, CNRS, Pl Eugene Bataillon, F-34095 Montpellier, France
来源：
TETRAHEDRON-ASYMMETRY | 2016年 / 27卷 / 01期
关键词：
DIASTEREOSELECTIVE REDUCTION; ASYMMETRIC-SYNTHESIS; ALDOL REACTIONS; CASSIA; (-)-DEOXOCASSINE; PROSOPIS; ROUTE; ENANTIODIVERGENT; CYCLOADDITION; DEBENZYLATION;
D O I：
10.1016/j.tetasy.2015.11.008
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
gamma-N,N-Dibenzylamino-beta-hydroxysulfoxide 1 proved to be an excellent chiral building block for the synthesis of a range of 1,2-amino alcohol-containing heterocycles. Thus, I was converted into 4,5-disubstuted oxazolidin-2-one 4 and aminoepoxides 2 and 3. Aminoepoxide 2 proved to be an excellent precursor to access oxazolidin-2-one 5 and azetidin-3-ol 6. Finally, 2 was used as a key intermediate that allowed the development of a divergent strategy to access cis-2-methyl-6-substituted piperidin-3-ol alkaloids. (+)-Deoxocassine 7 and a C-6 ethyl analogue 8 were prepared to illustrate this approach and to demonstrate that this strategy should be adaptable to the production of other members of this alkaloid family. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：22 / 30
页数：9
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