Literature DB >> 25215513

Oxidative 1,4-diamination of dienes using simple urea derivatives.

Devendar Anumandla1, Ryan Littlefield, Christopher S Jeffrey.   

Abstract

Diamination of alkenes and dienes has found widespread use in the synthesis of biologically active target molecules. Although the 1,2-diamination of alkenes has been comprehensively explored, versatile methods that install higher order 1,n-diamine moieties (e.g., n = 3-5) are not broadly developed. Herein, we report the development of an oxidative 1,4-diamination of dienes. This method represents one of the scarce examples of exclusive regioselectivity for 1,4-diamination. The reaction is easy to perform, uses simple reagents, works with a variety of functionalized dienes, and provides unique heterocyclic products.

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Year:  2014        PMID: 25215513     DOI: 10.1021/ol502460j

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  4 in total

1.  Generation and Reactivity of 2-Amido-1,3-diaminoallyl Cations: Cyclic Guanidine Annulations via Net (3 + 2) and (4 + 3) Cycloadditions.

Authors:  V Raghavendra Rao Kovvuri; Haoran Xue; Daniel Romo
Journal:  Org Lett       Date:  2020-02-03       Impact factor: 6.005

2.  Synthesis of Benzannulated Medium-ring Lactams via a Tandem Oxidative Dearomatization-Ring Expansion Reaction.

Authors:  Tezcan Guney; Todd A Wenderski; Matthew W Boudreau; Derek S Tan
Journal:  Chemistry       Date:  2018-08-02       Impact factor: 5.236

3.  Dearomative Indole (3 + 2) Reactions with Azaoxyallyl Cations--New Method for the Synthesis of Pyrroloindolines.

Authors:  Maria C DiPoto; Russell P Hughes; Jimmy Wu
Journal:  J Am Chem Soc       Date:  2015-11-17       Impact factor: 15.419

4.  Capture-Collapse Heterocyclization: 1,3-Diazepanes by C-N Reductive Elimination from Rhodacyclopentanones.

Authors:  Niall G McCreanor; Steven Stanton; John F Bower
Journal:  J Am Chem Soc       Date:  2016-09-02       Impact factor: 15.419

  4 in total

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