Photocatalytic Three-Component Umpolung Synthesis of 1,3-Diamines

被引：64

作者：

Rossolini, Thomas ^{[1
]}

Leitch, Jamie A. ^{[1
]}

Grainger, Rachel ^{[2
]}

Dixon, Darren J. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, 12 Mansfield Rd, Oxford OX1 3TA, England

[2] Astex Pharmaceut Ltd, 436 Cambridge Sci Pk,Milton Rd, Cambridge CB4 0QA, England

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 21期

关键词：

LIGHT PHOTOREDOX CATALYSIS; COUPLED ELECTRON-TRANSFER; C-H BONDS; VISIBLE-LIGHT; CARBONYL DERIVATIVES; ORGANIC-SYNTHESIS; AMINO-ALCOHOLS; RADICALS; HETEROARENES; ACTIVATION;

D O I：

10.1021/acs.orglett.8b02923

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A visible-light-mediated photocatalytic umpolung synthesis of 1,3-diamines from in situ-generated imines and dehydroalanine derivatives is described. Pivoting on a key nucleophilic addition of photocatalytically generated alpha-amino radicals to electron-deficient alkenes, this three-component coupling reaction affords 1,3-diamines efficiently and diastereoselectively. The mild protocol tolerates a wide variety of functionalities including heterocycles, pinacol boronates, and aliphatic chains. Application to biologically relevant alpha-amino-gamma-lactam demonstrated. synthesis and extension to 1,3-aminoalcohols is also demonstrated.

引用

页码：6794 / 6798

页数：5

共 46 条

[11] Reductive Amination by Photoredox Catalysis and Polarity-Matched Hydrogen Atom Transfer [J].