On the Asymmetric Induction in Proline-Catalyzed Aldol Reactions: Reagent-Controlled Addition Reactions of 2,2-Dimethyl-1,3-dioxane-5-one to Acyclic Chiral α-Branched Aldehydes

被引：7
作者：
Trajkovic, Jasna Marjanovic [1 ]
Milanovic, Vesna [2 ]
Ferjancic, Zorana [2 ]
Saicic, Radomir N. [2 ,3 ]
机构：
[1] Innovat Ctr, Fac Chem, Studentski Trg 16,POB 51, Belgrade 11158 118, Serbia
[2] Univ Belgrade, Fac Chem, Studentski Trg 16,POB 51, Belgrade 11158 118, Serbia
[3] Serbian Acad Arts & Sci, Knez Mihailova 35, Belgrade 11000, Serbia
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 41期
关键词：
Synthetic methods; Organocatalysis; Aldol reactions; Iminosugars; Diastereoselectivity; DE-NOVO SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; FABRY DISEASE; 1-DEOXYGALACTONOJIRIMYCIN; DIHYDROXYACETONE; ORGANOCATALYSIS; IMINOSUGARS; (+)-1-DEOXYGALACTONOJIRIMYCIN; 1-DEOXYNOJIRIMYCIN; BIOSYNTHESIS;
D O I：
10.1002/ejoc.201701073
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reagent stereocontrol in the proline-catalyzed aldol reaction of 2,2-dimethyl-1,3-dioxane-5-one 1 with chiral aldehydes has been investigated. Synthetically useful levels of diastereoselectivity could be achieved in reactions with acyclic chiral alpha-oxy and alpha-amino aldehydes in both matched and mismatched cases. By using this reaction as a key step, two medicinally relevant azasugars, 1-deoxy-galactonojirimycin (9) and 2,5-dideoxy-2,5-imino-d-altritol (10), were efficiently synthesized.
引用
收藏
页码：6146 / 6153
页数：8
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