Literature DB >> 25431651

Regioselective and Diastereoselective Aminoarylation of 1,3-Dienes.

Hongli Bao1, Liela Bayeh1, Uttam K Tambar1.   

Abstract

The 1,4-functionalization of dienes is a synthetically useful strategy for incorporating molecular complexity into a class of simple substrates. We report the aminoarylation of acyclic and cyclic 1,3-dienes via the sequential [4+2] cycloaddition with a sulfurdiimide reagent and copper-catalyzed allylic substitution with Grignard reagents. The regioselective and diastereoselective aminoarylation of unsymmetrical dienes is also presented, which highlights the utility of this method for generating products with multiple functional groups and stereocenters.

Entities:  

Year:  2014        PMID： 25431651      PMCID： PMC4242432          DOI： 10.1039/C4SC01152J

Source DB:  PubMed          Journal:  Chem Sci        ISSN： 2041-6520            Impact factor:   9.825


  20 in total

1.  Mechanism and regioselectivity of reductive elimination of pi-allylcopper (III) intermediates.

Authors:  Masahiro Yamanaka; Seiichi Kato; Eiichi Nakamura
Journal:  J Am Chem Soc       Date:  2004-05-26       Impact factor: 15.419

2.  Mechanisms of nucleophilic organocopper(I) reactions.

Authors:  Naohiko Yoshikai; Eiichi Nakamura
Journal:  Chem Rev       Date:  2011-11-23       Impact factor: 60.622

3.  Diamination of conjugated dienes and trienes catalyzed by N-heterocyclic carbene-pd(0) complexes.

Authors:  Liang Xu; Haifeng Du; Yian Shi
Journal:  J Org Chem       Date:  2007-08-04       Impact factor: 4.354

Review 4.  Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions.

Authors:  A Alexakis; J E Bäckvall; N Krause; O Pàmies; M Diéguez
Journal:  Chem Rev       Date:  2008-08-01       Impact factor: 60.622

Review 5.  Catalytic asymmetric conjugate addition and allylic alkylation with Grignard reagents.

Authors:  Syuzanna R Harutyunyan; Tim den Hartog; Koen Geurts; Adriaan J Minnaard; Ben L Feringa
Journal:  Chem Rev       Date:  2008-08       Impact factor: 60.622

6.  Allylic functionalization of unactivated olefins with Grignard reagents.

Authors:  Hongli Bao; Liela Bayeh; Uttam K Tambar
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-23       Impact factor: 15.336

7.  Mild two-step process for the transition-metal-free synthesis of carbon-carbon bonds from allylic alcohols/ethers and grignard reagents.

Authors:  Xinping Han; Yanhua Zhang; Jimmy Wu
Journal:  J Am Chem Soc       Date:  2010-03-31       Impact factor: 15.419

8.  Cu(I)-catalyzed diamination of conjugated dienes. Complementary regioselectivity from two distinct mechanistic pathways involving Cu(II) and Cu(III) species.

Authors:  Baoguo Zhao; Xingao Peng; Yingguang Zhu; Thomas A Ramirez; Richard G Cornwall; Yian Shi
Journal:  J Am Chem Soc       Date:  2011-12-02       Impact factor: 15.419

9.  Catalytic enantioselective allylic amination of unactivated terminal olefins via an ene reaction/[2,3]-rearrangement.

Authors:  Hongli Bao; Uttam K Tambar
Journal:  J Am Chem Soc       Date:  2012-10-29       Impact factor: 15.419

10.  Mechanism of copper(I)-catalyzed allylic alkylation of phosphorothioate esters: influence of the leaving group on α regioselectivity.

Authors:  Wenhao Sheng; Mian Wang; Matthias Lein; Linbin Jiang; Wanxing Wei; Jianyi Wang
Journal:  Chemistry       Date:  2013-09-03       Impact factor: 5.236
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  2 in total

1.  Copper-Catalyzed Aminothiolation of 1,3-Dienes via a Dihydrothiazine Intermediate.

Authors:  Christopher E Sleet; Uttam K Tambar
Journal:  Angew Chem Int Ed Engl       Date:  2017-04-13       Impact factor: 15.336

2.  Cycloadditions of Donor-Acceptor Cyclopropanes and -butanes using S=N-Containing Reagents: Access to Cyclic Sulfinamides, Sulfonamides, and Sulfinamidines.

Authors:  Gwyndaf A Oliver; Maximilian N Loch; André U Augustin; Pit Steinbach; Mohammed Sharique; Uttam K Tambar; Peter G Jones; Christoph Bannwarth; Daniel B Werz
Journal:  Angew Chem Int Ed Engl       Date:  2021-10-29       Impact factor: 16.823
  2 in total

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