Literature DB >> 16089447

Copper(II) acetate promoted intramolecular diamination of unactivated olefins.

Thomas P Zabawa1, Dhanalakshmi Kasi, Sherry R Chemler.   

Abstract

A concise method for the synthesis of cyclic sulfamides and vicinal diamines is presented. This method is enabled by Cu(OAc)2 and demonstrates a new transformation for this metal. Both five- and six-membered vicinal diamine-containing heterocycles have been synthesized in good to excellent yields, and substrate-based asymmetric induction has been achieved. This is the first reported example of intramolecular diamination of olefins.

Entities:  

Year:  2005        PMID: 16089447     DOI: 10.1021/ja053335v

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  47 in total

1.  Complementary regioselectivity in the Cu(I)-catalyzed diamination of conjugated dienes to form cyclic sulfamides.

Authors:  Richard G Cornwall; Baoguo Zhao; Yian Shi
Journal:  Org Lett       Date:  2010-12-30       Impact factor: 6.005

2.  The enantioselective intramolecular aminative functionalization of unactivated alkenes, dienes, allenes and alkynes for the synthesis of chiral nitrogen heterocycles.

Authors:  Sherry R Chemler
Journal:  Org Biomol Chem       Date:  2009       Impact factor: 3.876

3.  syn-1,2-Amino alcohols via diastereoselective allylic C-H amination.

Authors:  Kenneth J Fraunhoffer; M Christina White
Journal:  J Am Chem Soc       Date:  2007-05-22       Impact factor: 15.419

4.  Photocatalytic Oxyamination of Alkenes: Copper(II) Salts as Terminal Oxidants in Photoredox Catalysis.

Authors:  Nicholas L Reed; Madeline I Herman; Vladimir P Miltchev; Tehshik P Yoon
Journal:  Org Lett       Date:  2018-11-08       Impact factor: 6.005

5.  A palladium-catalyzed dehydrogenative diamination of terminal olefins.

Authors:  Bin Wang; Haifeng Du; Yian Shi
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  Stereoselective Synthesis of Cyclic Guanidines by Directed Diamination of Unactivated Alkenes.

Authors:  Artur K Mailyan; Kyle Young; Joanna L Chen; Bradley T Reid; Armen Zakarian
Journal:  Org Lett       Date:  2016-10-25       Impact factor: 6.005

7.  Palladium-catalyzed enantioselective addition of two distinct nucleophiles across alkenes capable of quinone methide formation.

Authors:  Katrina H Jensen; Tejas P Pathak; Yang Zhang; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2009-12-02       Impact factor: 15.419

8.  Influence of catalyst structure and reaction conditions on anti- versus syn-aminopalladation pathways in Pd-catalyzed alkene carboamination reactions of N-allylsulfamides.

Authors:  Ryan M Fornwald; Jonathan A Fritz; John P Wolfe
Journal:  Chemistry       Date:  2014-06-17       Impact factor: 5.236

9.  Gold(I)-catalyzed intramolecular dihydroamination of allenes with N,N'-disubstituted ureas to form bicyclic imidazolidin-2-ones.

Authors:  Hao Li; Ross A Widenhoefer
Journal:  Org Lett       Date:  2009-06-18       Impact factor: 6.005

10.  Stereoselective Synthesis of Saturated Heterocycles via Pd-Catalyzed Alkene Carboetherification and Carboamination Reactions.

Authors:  John P Wolfe
Journal:  Synlett       Date:  2006-11-13       Impact factor: 2.454

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