Literature DB >> 31433174

Enantioselective, Lewis Base-Catalyzed, Intermolecular Sulfenoamination of Alkenes.

Aaron Roth1, Scott E Denmark1.   

Abstract

A method for the catalytic, enantioselective, intermolecular, 1,2-sulfenoamination of alkenes is described. Functionalization is achieved through the intermediacy of an enantioenriched, configurationally stable thiiranium ion generated by Lewis base activation of a readily available sulfur electrophile. A diverse set of anilines and benzylamines react with different styrenes to afford products in good yield and stereoselectivity. Downstream manipulation of the products is facilitated by deprotonation of the amines to enable carbon-sulfur bond cleavage.

Entities:  

Year:  2019        PMID： 31433174      PMCID： PMC6876745          DOI： 10.1021/jacs.9b07019

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


  22 in total

1.  Advances in homogeneous and heterogeneous catalytic asymmetric epoxidation.

Authors:  Q-H Xia; H-Q Ge; C-P Ye; Z-M Liu; K-X Su
Journal:  Chem Rev       Date:  2005-05       Impact factor: 60.622

2.  Diaryl Selenide Catalyzed Vicinal Trifluoromethylthioamination of Alkenes.

Authors:  Jie Luo; Zechen Zhu; Yannan Liu; Xiaodan Zhao
Journal:  Org Lett       Date:  2015-07-09       Impact factor: 6.005

3.  Enantioselective, Lewis Base-Catalyzed Carbosulfenylation of Alkenylboronates by 1,2-Boronate Migration.

Authors:  Zhonglin Tao; Kevin A Robb; Jesse L Panger; Scott E Denmark
Journal:  J Am Chem Soc       Date:  2018-11-09       Impact factor: 15.419

4.  Catalytic asymmetric thiofunctionalization of unactivated alkenes.

Authors:  Scott E Denmark; David J P Kornfilt; Thomas Vogler
Journal:  J Am Chem Soc       Date:  2011-09-14       Impact factor: 15.419

Review 5.  Catalytic, asymmetric halofunctionalization of alkenes--a critical perspective.

Authors:  Scott E Denmark; William E Kuester; Matthew T Burk
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-25       Impact factor: 15.336

6.  Diastereoselective Synthesis of syn-β-Lactams Using Rh-Catalyzed Reductive Mannich-Type Reaction of α,β-Unsaturated Esters.

Authors:  Motoyuki Isoda; Kazuyuki Sato; Masato Funakoshi; Keiko Omura; Atsushi Tarui; Masaaki Omote; Akira Ando
Journal:  J Org Chem       Date:  2015-08-07       Impact factor: 4.354

7.  Concise enantioselective total synthesis of neopeltolide macrolactone highlighted by ether transfer.

Authors:  Rendy Kartika; Thomas R Gruffi; Richard E Taylor
Journal:  Org Lett       Date:  2008-10-15       Impact factor: 6.005

8.  Synthesis and reactivity of enantiomerically enriched thiiranium ions.

Authors:  Scott E Denmark; Thomas Vogler
Journal:  Chemistry       Date:  2009-11-02       Impact factor: 5.236

9.  Lewis base catalyzed, enantioselective, intramolecular sulfenoamination of olefins.

Authors:  Scott E Denmark; Hyung Min Chi
Journal:  J Am Chem Soc       Date:  2014-06-13       Impact factor: 15.419

10.  Catalytic, Enantioselective, Intramolecular Sulfenoamination of Alkenes with Anilines.

Authors:  Scott E Denmark; Hyung Min Chi
Journal:  J Org Chem       Date:  2017-03-15       Impact factor: 4.354
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  6 in total

1.  Enantioselective Synthesis of γ-Lactams by Lewis Base Catalyzed Sulfenoamidation of Alkenes.

Authors:  Jesse L Panger; Scott E Denmark
Journal:  Org Lett       Date:  2019-12-20       Impact factor: 6.005

Review 2.  Catalytic, Enantioselective Sulfenofunctionalization of Alkenes: Development and Recent Advances.

Authors:  Anastassia Matviitsuk; Jesse L Panger; Scott E Denmark
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-18       Impact factor: 15.336

Review 3.  Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors:  Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal:  Chem Rev       Date:  2021-11-23       Impact factor: 60.622

4.  Directed, nickel-catalyzed 1,2-alkylsulfenylation of alkenyl carbonyl compounds.

Authors:  Zi-Qi Li; Wen-Ji He; Hui-Qi Ni; Keary M Engle
Journal:  Chem Sci       Date:  2022-05-02       Impact factor: 9.969

5.  Metal-free synthesis of 1,4-benzodiazepines and quinazolinones from hexafluoroisopropyl 2-aminobenzoates at room temperature.

Authors:  Jiewen Chen; En Liang; Jie Shi; Yinrong Wu; Kangmei Wen; Xingang Yao; Xiaodong Tang
Journal:  RSC Adv       Date:  2021-01-28       Impact factor: 3.361

6.  Ritter-enabled catalytic asymmetric chloroamidation of olefins.

Authors:  Daniel C Steigerwald; Bardia Soltanzadeh; Aritra Sarkar; Cecilia C Morgenstern; Richard J Staples; Babak Borhan
Journal:  Chem Sci       Date:  2020-12-07       Impact factor: 9.825
  6 in total

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