Literature DB >> 22352383

Stereoselective synthesis of cis-2,5-disubstituted pyrrolidines via Wacker-type aerobic oxidative cyclization of alkenes with tert-butanesulfinamide nucleophiles.

Joanne E Redford1, Richard I McDonald, Matthew L Rigsby, Joshua D Wiensch, Shannon S Stahl.   

Abstract

Palladium(II)-catalyzed aerobic oxidative cyclization of alkenes with tethered tert-butanesulfinamides furnishes enantiopure 2,5-disubstituted pyrrolidines, originating from readily available and easily diversified starting materials. These reactions are the first reported examples of metal-catalyzed addition of sulfinamide nucleophiles to alkenes.
© 2012 American Chemical Society

Entities:  

Mesh：

Substances：

Year:  2012        PMID： 22352383      PMCID： PMC3298084          DOI： 10.1021/ol3000519

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


  43 in total

1.  2,5-Disubstituted pyrrolidines: synthesis by enamine reduction and subsequent regioselective and diastereoselective alkylations.

Authors:  Syed Raziullah Hussaini; Mark G Moloney
Journal:  Org Biomol Chem       Date:  2006-05-31       Impact factor: 3.876

2.  cis-2,5-dicyanopyrrolidine inhibitors of dipeptidyl peptidase IV: synthesis and in vitro, in vivo, and X-ray crystallographic characterization.

Authors:  Stephen W Wright; Mark J Ammirati; Kim M Andrews; Anne M Brodeur; Dennis E Danley; Shawn D Doran; Jay S Lillquist; Lester D McClure; R Kirk McPherson; Stephen J Orena; Janice C Parker; Jana Polivkova; Xiayang Qiu; Walter C Soeller; Carolyn B Soglia; Judith L Treadway; Maria A VanVolkenburg; Hong Wang; Donald C Wilder; Thanh V Olson
Journal:  J Med Chem       Date:  2006-06-01       Impact factor: 7.446

3.  Pd-catalyzed carboamination of oxazolidin-2-ones: a stereoselective route to trans-2,5-disubstituted pyrrolidines.

Authors:  Georgia S Lemen; John P Wolfe
Journal:  Org Lett       Date:  2010-05-21       Impact factor: 6.005

4.  Asymmetric palladium-catalyzed carboamination reactions for the synthesis of enantiomerically enriched 2-(arylmethyl)- and 2-(alkenylmethyl)pyrrolidines.

Authors:  Duy N Mai; John P Wolfe
Journal:  J Am Chem Soc       Date:  2010-09-08       Impact factor: 15.419

5.  A concise asymmetric route to the bridged bicyclic tropane alkaloid ferruginine using enyne ring-closing metathesis.

Authors:  Varinder K Aggarwal; Christopher J Astle; Mark Rogers-Evans
Journal:  Org Lett       Date:  2004-04-29       Impact factor: 6.005

6.  Synthesis of heterocycles via palladium pi-olefin and pi-alkyne chemistry.

Authors:  Gilson Zeni; Richard C Larock
Journal:  Chem Rev       Date:  2004-05       Impact factor: 60.622

Review 7.  Palladium oxidase catalysis: selective oxidation of organic chemicals by direct dioxygen-coupled turnover.

Authors:  Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2004-06-28       Impact factor: 15.336

8.  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

9.  General strategy for the construction of enantiopure pyrrolidine-based alkaloids. Total synthesis of (-)-monomorine.

Authors:  Suhong Zhang; Liang Xu; Lei Miao; Hong Shu; Mark L Trudell
Journal:  J Org Chem       Date:  2007-03-16       Impact factor: 4.354

10.  Palladium-catalyzed aerobic oxidative amination of alkenes: development of intra- and intermolecular aza-Wacker reactions.

Authors:  Vasily Kotov; Christopher C Scarborough; Shannon S Stahl
Journal:  Inorg Chem       Date:  2007-03-19       Impact factor: 5.165
View more
  5 in total

1.  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

2.  Catalytic Asymmetric Synthesis of Chiral γ-Amino Ketones via Umpolung Reactions of Imines.

Authors:  Lin Hu; Yongwei Wu; Zhe Li; Li Deng
Journal:  J Am Chem Soc       Date:  2016-11-30       Impact factor: 15.419

3.  Diastereoselective C-H Bond Amination for Disubstituted Pyrrolidines.

Authors:  Diana A Iovan; Matthew J T Wilding; Yunjung Baek; Elisabeth T Hennessy; Theodore A Betley
Journal:  Angew Chem Int Ed Engl       Date:  2017-11-08       Impact factor: 15.336

Review 4.  Applications of tert-butanesulfinamide in the synthesis of N-heterocycles via sulfinimines.

Authors:  Rose Mary Philip; Sankaran Radhika; P V Saranya; Gopinathan Anilkumar
Journal:  RSC Adv       Date:  2020-11-23       Impact factor: 4.036

Review 5.  N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles.

Authors:  Joseane A Mendes; Paulo R R Costa; Miguel Yus; Francisco Foubelo; Camilla D Buarque
Journal:  Beilstein J Org Chem       Date:  2021-05-12       Impact factor: 2.883
  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.