Literature DB >> 24938206

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

Ryan M Fornwald1, Jonathan A Fritz, John P Wolfe.   

Abstract

The Pd-catalyzed coupling of N-allylsulfamides with aryl and alkenyl triflates to afford cyclic sulfamide products is described. In contrast to other known Pd-catalyzed alkene carboamination reactions, these transformations may be selectively induced to occur by way of either anti- or syn-aminopalladation mechanistic pathways by modifying the catalyst structure and reaction conditions.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  addition reactions; alkenes; heterocycles; palladium; stereoselectivity

Mesh:

Substances:

Year:  2014        PMID: 24938206      PMCID: PMC4102893          DOI: 10.1002/chem.201402258

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  37 in total

1.  Cyclosulfamide-based derivatives as inhibitors of noroviruses.

Authors:  Dengfeng Dou; Sivakoteswara R Mandadapu; Kevin R Alliston; Yunjeong Kim; Kyeong-Ok Chang; William C Groutas
Journal:  Eur J Med Chem       Date:  2011-10-20       Impact factor: 6.514

2.  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

3.  A new synthesis of imidazolidin-2-ones via Pd-catalyzed carboamination of N-allylureas.

Authors:  Jonathan A Fritz; Josephine S Nakhla; John P Wolfe
Journal:  Org Lett       Date:  2006-06-08       Impact factor: 6.005

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

Authors:  Thomas P Zabawa; Dhanalakshmi Kasi; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2005-08-17       Impact factor: 15.419

Review 5.  Biaryl phosphane ligands in palladium-catalyzed amination.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  Palladium-catalyzed synthesis of N-aryl pyrrolidines from gamma-(N-Arylamino) alkenes: evidence for chemoselective alkene insertion into Pd--N bonds.

Authors:  Joshua E Ney; John P Wolfe
Journal:  Angew Chem Int Ed Engl       Date:  2004-07-05       Impact factor: 15.336

7.  Mechanistic studies of Wacker-type amidocyclization of alkenes catalyzed by (IMes)Pd(TFA)2(H2O): kinetic and stereochemical implications of proton transfer.

Authors:  Xuan Ye; Paul B White; Shannon S Stahl
Journal:  J Org Chem       Date:  2012-11-30       Impact factor: 4.354

8.  Synthesis and antibacterial activities of novel oxazolidinones having cyclic sulfonamide moieties.

Authors:  Seong Jong Kim; Seoung Jong Kim; Myung-Ho Jung; Kyung Ho Yoo; Jung-Hyuck Cho; Chang-Hyun Oh
Journal:  Bioorg Med Chem Lett       Date:  2008-09-11       Impact factor: 2.823

9.  Mechanism of N-fluorobenzenesulfonimide promoted diamination and carboamination reactions: divergent reactivity of a Pd(IV) species.

Authors:  Paul A Sibbald; Carolyn F Rosewall; Rodney D Swartz; Forrest E Michael
Journal:  J Am Chem Soc       Date:  2009-11-04       Impact factor: 15.419

10.  Mild conditions for Pd-catalyzed carboamination of N-protected hex-4-enylamines and 1-, 3-, and 4-substituted pent-4-enylamines. Scope, limitations, and mechanism of pyrrolidine formation.

Authors:  Myra Beaudoin Bertrand; Joshua D Neukom; John P Wolfe
Journal:  J Org Chem       Date:  2008-10-23       Impact factor: 4.354

View more
  17 in total

1.  Asymmetric Pd-Catalyzed Alkene Carboamination Reactions for the Synthesis of 2-Aminoindane Derivatives.

Authors:  Derick R White; Johnathon T Hutt; John P Wolfe
Journal:  J Am Chem Soc       Date:  2015-08-27       Impact factor: 15.419

2.  Synthesis of Polycyclic Nitrogen Heterocycles via Cascade Pd-Catalyzed Alkene Carboamination/Diels-Alder Reactions.

Authors:  Derick R White; John P Wolfe
Journal:  Org Lett       Date:  2015-05-06       Impact factor: 6.005

3.  Recent Developments in Pd(0)-Catalyzed Alkene Carboheterofunctionalization Reactions.

Authors:  Zachary J Garlets; Derick R White; John P Wolfe
Journal:  Asian J Org Chem       Date:  2017-03-10       Impact factor: 3.319

4.  Synthesis of Cyclic Guanidines Bearing N-Arylsulfonyl and N-Cyano Protecting Groups via Pd-Catalyzed Alkene Carboamination Reactions.

Authors:  Luke J Peterson; Jingyi Luo; John P Wolfe
Journal:  Org Lett       Date:  2017-05-23       Impact factor: 6.005

5.  Palladium-Catalyzed Alkene Carboamination Reactions of Electron-Poor Nitrogen Nucleophiles.

Authors:  Luke J Peterson; John P Wolfe
Journal:  Adv Synth Catal       Date:  2015-07-14       Impact factor: 5.837

6.  Asymmetric Palladium-Catalyzed Alkene Carboamination Reactions for the Synthesis of Cyclic Sulfamides.

Authors:  Zachary J Garlets; Kaia R Parenti; John P Wolfe
Journal:  Chemistry       Date:  2016-03-10       Impact factor: 5.236

7.  Pd-Catalyzed C-C, C-N, and C-O Bond-Forming Difunctionalization Reactions of Alkenes Bearing Tethered Aryl/Alkenyl Triflates.

Authors:  Derick R White; Evan C Bornowski; John P Wolfe
Journal:  Isr J Chem       Date:  2020-01-24       Impact factor: 3.333

8.  Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction.

Authors:  Scott A Shuler; Guoyin Yin; Sarah B Krause; Caroline M Vesper; Donald A Watson
Journal:  J Am Chem Soc       Date:  2016-10-18       Impact factor: 15.419

9.  Synthesis of Cyclic Guanidines via Silver-Catalyzed Intramolecular Alkene Hydroamination Reactions of N-Allylguanidines.

Authors:  Zachary J Garlets; Mattia Silvi; John P Wolfe
Journal:  Org Lett       Date:  2016-05-11       Impact factor: 6.005

10.  Stereocontrolled synthesis of bicyclic ureas and sulfamides via Pd-catalyzed alkene carboamination reactions.

Authors:  Nicholas R Babij; Jordan R Boothe; Grace M McKenna; Ryan M Fornwald; John P Wolfe
Journal:  Tetrahedron       Date:  2019-04-20       Impact factor: 2.457

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.