Literature DB >> 21913287

Enantioselective intramolecular benzylic C-H bond amination: efficient synthesis of optically active benzosultams.

Masami Ichinose1, Hidehiro Suematsu, Yoichi Yasutomi, Yota Nishioka, Tatsuya Uchida, Tsutomu Katsuki.   

Abstract

'Salen' along: the iridium(III)-salen complex 1 efficiently catalyzes the title reaction of 2-ethylbenzenesulfonyl azides to give five-membered sultams with high enantioselectivity. Other 2-alkyl-substitued substrates lead to five- and six-membered sultams with high enantioselectivity; the regioselectivity depends upon the substrate and the catalyst used. EDG=electron-donating group.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2011        PMID： 21913287     DOI： 10.1002/anie.201101801

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  18 in total

1.  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

2.  Heterocycle synthesis via direct C-H/N-H coupling.

Authors:  Enrico T Nadres; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2011-12-29       Impact factor: 15.419

3.  Directed amination of non-acidic arene C-H bonds by a copper-silver catalytic system.

Authors:  Ly Dieu Tran; James Roane; Olafs Daugulis
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-24       Impact factor: 15.336

4.  Metal-Catalyzed and Metal-Free Intermolecular Amination of Light Alkanes and Benzenes.

Authors:  Pericles Stavropoulos
Journal:  Comments Mod Chem A Comments Inorg Chem       Date:  2016-04-29       Impact factor: 4.533

5.  Synthesis of diverse pyrazole-4-sulfonyl chlorides starting from 2-(benzylthio)malonaldehyde.

Authors:  Pavlo A Sokolyuk; Ivan S Kondratov; Olexiy V Gavrylenko; Andrey A Tolmachov
Journal:  Mol Divers       Date:  2015-09-12       Impact factor: 2.943

6.  Enantioselective intramolecular C-H amination catalyzed by engineered cytochrome P450 enzymes in vitro and in vivo.

Authors:  John A McIntosh; Pedro S Coelho; Christopher C Farwell; Z Jane Wang; Jared C Lewis; Tristan R Brown; Frances H Arnold
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-24       Impact factor: 15.336

7.  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

8.  Intramolecular C(sp(3))H amination of arylsulfonyl azides with engineered and artificial myoglobin-based catalysts.

Authors:  Melanie Bordeaux; Ritesh Singh; Rudi Fasan
Journal:  Bioorg Med Chem       Date:  2014-05-20       Impact factor: 3.641

9.  Enantioselective Radical Construction of 5-Membered Cyclic Sulfonamides by Metalloradical C-H Amination.

Authors:  Yang Hu; Kai Lang; Chaoqun Li; Joseph B Gill; Isaac Kim; Hongjian Lu; Kimberly B Fields; McKenzie Marshall; Qigan Cheng; Xin Cui; Lukasz Wojtas; X Peter Zhang
Journal:  J Am Chem Soc       Date:  2019-11-01       Impact factor: 15.419

10.  P450-catalyzed intramolecular sp3 C-H amination with arylsulfonyl azide substrates.

Authors:  Ritesh Singh; Melanie Bordeaux; Rudi Fasan
Journal:  ACS Catal       Date:  2014-01-06       Impact factor: 13.084
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