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Asymmetric synthesis of (1S,2R)-2-aminocyclooctanecarboxylic acid
Tetrahedron: Asymmetry Pub Date : 12 December 2008 , DOI: 10.1016/j.tetasy.2008.12.018 Narciso M. Garrido , Magda Blanco , Imanol F. Cascón , David Díez , Victor M. Vicente , Francisca Sanz , Julio G. Urones
Tetrahedron: Asymmetry Pub Date : 12 December 2008 , DOI: 10.1016/j.tetasy.2008.12.018 Narciso M. Garrido , Magda Blanco , Imanol F. Cascón , David Díez , Victor M. Vicente , Francisca Sanz , Julio G. Urones
A highly efficient asymmetric synthesis of (1S,2R)-2-aminocyclooctanecarboxylic acid has been completed. This asymmetric synthesis using cycloocta-1,5-diene as the starting material is achieved in 77% yield via a four-step sequence from tert-butyl cycloocta-1,7-dienecarboxylate 10 where the extra double bond adjacent to the unsaturated ester is essential to improve the yield. Furthermore, the Michael adduct intermediate (1S,2R,αR)-14 could be used towards the synthesis of the natural product tashiromine.
中文翻译:
(1 S,2 R)-2-氨基环辛烷羧酸的不对称合成
(1 S,2 R)-2-氨基环辛烷羧酸的高效不对称合成已经完成。使用环辛基-1,5-二烯作为起始原料的这种不对称合成反应可通过四步法从环丁基-1,7-二烯羧酸叔丁酯10中按四个步骤进行,其中邻近不饱和酯的额外双键为对提高产量至关重要。此外,Michael加合物的中间体(1小号,2 - [R,α - [R )- 14可朝向天然产物tashiromine的合成中使用。
更新日期:2017-01-31
中文翻译:
(1 S,2 R)-2-氨基环辛烷羧酸的不对称合成
(1 S,2 R)-2-氨基环辛烷羧酸的高效不对称合成已经完成。使用环辛基-1,5-二烯作为起始原料的这种不对称合成反应可通过四步法从环丁基-1,7-二烯羧酸叔丁酯10中按四个步骤进行,其中邻近不饱和酯的额外双键为对提高产量至关重要。此外,Michael加合物的中间体(1小号,2 - [R,α - [R )- 14可朝向天然产物tashiromine的合成中使用。