Literature DB >> 21919470

Stereoselective rhodium-catalyzed amination of alkenes.

Hélène Lebel1, Cédric Spitz, Olivier Leogane, Carl Trudel, Michaël Parmentier.   

Abstract

The first stereoselective rhodium-catalyzed intermolecular aziridination and C-H amination of alkenes to produce chiral carbamate-protected aziridines and allylic amines is described. Good yields and diastereoselectivities were achieved using a readily available chiral N-tosyloxycarbamate and stoichiometric amount of the alkene substrate. Furthermore the protecting group is easy to cleave under mild reaction conditions.
© 2011 American Chemical Society

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Year:  2011        PMID: 21919470     DOI: 10.1021/ol2021516

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


  14 in total

1.  Chemo- and Enantioselective Intramolecular Silver-Catalyzed Aziridinations.

Authors:  Minsoo Ju; Cale D Weatherly; Ilia A Guzei; Jennifer M Schomaker
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-12       Impact factor: 15.336

2.  Mechanism and Dynamics of Intramolecular C-H Insertion Reactions of 1-Aza-2-azoniaallene Salts.

Authors:  Xin Hong; Daniel A Bercovici; Zhongyue Yang; Nezar Al-Bataineh; Ramya Srinivasan; Ram C Dhakal; K N Houk; Matthias Brewer
Journal:  J Am Chem Soc       Date:  2015-07-07       Impact factor: 15.419

3.  Application of diazene-directed fragment assembly to the total synthesis and stereochemical assignment of (+)-desmethyl-meso-chimonanthine and related heterodimeric alkaloids.

Authors:  Stephen P Lathrop; Mohammad Movassaghi
Journal:  Chem Sci       Date:  2014-01-01       Impact factor: 9.825

4.  Regioselective differentiation of vicinal methylene C-H bonds enabled by silver-catalysed nitrene transfer.

Authors:  Ryan J Scamp; Bradley Scheffer; Jennifer M Schomaker
Journal:  Chem Commun (Camb)       Date:  2019-06-20       Impact factor: 6.222

5.  Catalyst-Controlled and Tunable, Chemoselective Silver-Catalyzed Intermolecular Nitrene Transfer: Experimental and Computational Studies.

Authors:  Nicholas S Dolan; Ryan J Scamp; Tzuhsiung Yang; John F Berry; Jennifer M Schomaker
Journal:  J Am Chem Soc       Date:  2016-10-26       Impact factor: 15.419

6.  Late-Stage Intermolecular Allylic C-H Amination.

Authors:  Takafumi Ide; Kaibo Feng; Charlie F Dixon; Dawei Teng; Joseph R Clark; Wei Han; Chloe I Wendell; Vanessa Koch; M Christina White
Journal:  J Am Chem Soc       Date:  2021-09-13       Impact factor: 15.419

7.  Rh2(II)-Catalyzed Intermolecular N-Aryl Aziridination of Olefins Using Nonactivated N Atom Precursors.

Authors:  Tianning Deng; Wrickban Mazumdar; Yuki Yoshinaga; Pooja B Patel; Dana Malo; Tala Malo; Donald J Wink; Tom G Driver
Journal:  J Am Chem Soc       Date:  2021-11-08       Impact factor: 15.419

8.  Copper-catalyzed oxidative amination and allylic amination of alkenes.

Authors:  Timothy W Liwosz; Sherry R Chemler
Journal:  Chemistry       Date:  2013-07-22       Impact factor: 5.236

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.  Simultaneous structure-activity studies and arming of natural products by C-H amination reveal cellular targets of eupalmerin acetate.

Authors:  Jing Li; Justin S Cisar; Cong-Ying Zhou; Brunilda Vera; Howard Williams; Abimael D Rodríguez; Benjamin F Cravatt; Daniel Romo
Journal:  Nat Chem       Date:  2013-05-19       Impact factor: 24.427

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