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Iron-Catalyzed Diastereoselective Synthesis of Disubstituted Morpholines via C–O or C–N Bond Formation
Synlett ( IF 1.7 ) Pub Date : 2020-07-23 , DOI: 10.1055/s-0040-1707902
Janine Cossy , Thomas Aubineau , Alexandre Dupas , Tian Zeng

The diastereoselective synthesis of 2,6- and 3,5-disubstituted morpholines was achieved from 1,2-amino ethers and 1,2-hydroxy amines substituted by an allylic alcohol using an iron(III) catalyst. The morpholines were obtained either by C–O or C–N bond formation. A plausible mechanism is suggested, involving a thermodynamic equilibrium to explain the formation of the cis diastereoisomer as the major product.

中文翻译:

铁催化通过 C-O 或 C-N 键形成双取代吗啉的非对映选择性合成

2,6-和3,5-二取代吗啉的非对映选择性合成是使用铁(III)催化剂从烯丙醇取代的1,2-氨基醚和1,2-羟基胺实现的。吗啉是通过 C-O 或 C-N 键形成获得的。提出了一个合理的机制,涉及热力学平衡来解释作为主要产物的顺式非对映异构体的形成。
更新日期:2020-07-23
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