Catalytic asymmetric synthesis of 1,2-diamines,Chemical Society Reviews

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Catalytic asymmetric synthesis of 1,2-diamines
Chemical Society Reviews ( IF 40.4 ) Pub Date : 2024-07-11 , DOI: 10.1039/d3cs00379e
Francisco Foubelo _{1,

2} , Carmen Nájera ₂ , Ma Gracia Retamosa _{1,

2} , José M Sansano _{1,

2} , Miguel Yus ₂

Affiliation

The asymmetric catalytic synthesis of 1,2-diamines has received considerable interest, especially in the last ten years, due to their presence in biologically active compounds and their applications for the development of synthetic building blocks, chiral ligands and organocatalysts. Synthetic strategies based on C–N bond-forming reactions involve mainly (a) ring opening of aziridines and azabenzonorbornadienes, (b) hydroamination of allylic amines, (c) hydroamination of enamines and (d) diamination of olefins. In the case of C–C bond-forming reactions are included (a) the aza-Mannich reaction of imino esters, imino nitriles, azlactones, isocyano acetates, and isothiocyanates with imines, (b) the aza-Henry reaction of nitroalkanes with imines, (c) imine–imine coupling reactions, and (d) reductive coupling of enamines with imines, and (e) [3+2] cycloaddition with imines. C–H bond forming reactions include hydrogenation of C [double bond, length as m-dash]

N bonds and C–H amination reactions. Other catalytic methods include desymmetrization reactions of meso-diamines.

中文翻译：

1,2-二胺的催化不对称合成

1,2-二胺的不对称催化合成引起了人们的极大兴趣，特别是在过去十年中，因为它们存在于生物活性化合物中，并且在开发合成结构单元、手性配体和有机催化剂方面具有应用。基于C-N键形成反应的合成策略主要涉及（a）氮丙啶和氮杂苯并降冰片二烯的开环，（b）烯丙胺的加氢胺化，（c）烯胺的加氢胺化和（d）烯烃的二胺化。就 C-C 键形成反应而言，包括 (a) 亚氨基酯、亚氨基腈、吖内酯、异氰酸酯和异硫氰酸酯与亚胺的氮杂-曼尼希反应，(b) 硝基烷烃与亚胺的氮杂-亨利反应，（c）亚胺-亚胺偶联反应，（d）烯胺与亚胺的还原偶联，以及（e）与亚胺的[3+2]环加成反应。 C-H键形成反应包括C的氢化

N键和C-H胺化反应。其他催化方法包括内消旋二胺的去对称反应。

更新日期：2024-07-11

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