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Literature DB >> 23597174

Catalytic, enantioselective, intramolecular carbosulfenylation of olefins.

Abstract

The first catalytic, enantioselective carbosulfenylation of alkenes with an aromatic nucleophile is described, using a BINAM-based selenophosphoramide catalyst. E-Alkyl- and aryl-substituted alkenes afforded tetrahydronaphthalenes with complete diastereospecificity, and generally high enantiomeric ratios.

Entities: CellLine Chemical Disease

Mesh：

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Year: 2013 PMID： 23597174 PMCID： PMC3675264 DOI： 10.1021/ja401867b

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

18 in total

1. Lewis base catalysis in organic synthesis.

Authors: Scott E Denmark; Gregory L Beutner
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

2. Lewis base activation of Lewis acids: development of a Lewis base catalyzed selenolactonization.

Authors: Scott E Denmark; William R Collins
Journal: Org Lett Date: 2007-08-17 Impact factor: 6.005

3. Highly enantioselective sulfenylation of beta-ketoesters: H-bond acceptor catalysis.

Authors: Ling Fang; Aijun Lin; Hongwen Hu; Chengjian Zhu
Journal: Chemistry Date: 2009-07-20 Impact factor: 5.236

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

5. Preparative and mechanistic studies toward the rational development of catalytic, enantioselective selenoetherification reactions.

Authors: Scott E Denmark; Dipannita Kalyani; William R Collins
Journal: J Am Chem Soc Date: 2010-11-10 Impact factor: 15.419

6. Enantioselective organocatalytic alpha-sulfenylation of substituted diketopiperazines.

Authors: Nathan W Polaske; Ramin Dubey; Gary S Nichol; Bogdan Olenyuk
Journal: Tetrahedron Asymmetry Date: 2009-12-11

7. Organocatalytic, asymmetric synthesis of 3-sulfenylated N-Boc-protected oxindoles.

Authors: Chuan Wang; Xuena Yang; Charles C J Loh; Gerhard Raabe; Dieter Enders
Journal: Chemistry Date: 2012-07-26 Impact factor: 5.236

8. Observation of direct sulfenium and selenenium group transfer from thiiranium and seleniranium ions to alkenes.

Authors: Scott E Denmark; William R Collins; Matthew D Cullen
Journal: J Am Chem Soc Date: 2009-03-18 Impact factor: 15.419

9. Chiral anion-mediated asymmetric ring opening of meso-aziridinium and episulfonium ions.

Authors: Gregory L Hamilton; Toshio Kanai; F Dean Toste
Journal: J Am Chem Soc Date: 2008-10-21 Impact factor: 15.419

10. Catalytic Alkene Cyclization Reactions for the Stereoselective Synthesis of Complex "Terpenoid-like" Heterocycles.

Authors: Jared T Moore; Cristian Soldi; James C Fettinger; Jared T Shaw
Journal: Chem Sci Date: 2012-10-25 Impact factor: 9.825

20 in total

1. (R)-N,N'-Dimethyl-1,1'-binaphthyldiamine.

Authors: Scott E Denmark; Pavel G Ryabchuk
Journal: Organic Synth Date: 2019-09-27

2. Structural, Mechanistic, Spectroscopic, and Preparative Studies on the Lewis Base Catalyzed, Enantioselective Sulfenofunctionalization of Alkenes.

Authors: Eduard Hartmann; Scott E Denmark
Journal: Helv Chim Acta Date: 2017-09-14 Impact factor: 2.164

10. Investigating the Enantiodetermining Step of a Chiral Lewis Base Catalyzed Bromocycloetherification of Privileged Alkenes.

Authors: Dietrich Böse; Scott E Denmark
Journal: Synlett Date: 2017-11-13 Impact factor: 2.454

Catalytic, enantioselective, intramolecular carbosulfenylation of olefins.

1. Lewis base catalysis in organic synthesis.

2. Lewis base activation of Lewis acids: development of a Lewis base catalyzed selenolactonization.

3. Highly enantioselective sulfenylation of beta-ketoesters: H-bond acceptor catalysis.

4. Catalytic asymmetric thiofunctionalization of unactivated alkenes.

5. Preparative and mechanistic studies toward the rational development of catalytic, enantioselective selenoetherification reactions.

6. Enantioselective organocatalytic alpha-sulfenylation of substituted diketopiperazines.

7. Organocatalytic, asymmetric synthesis of 3-sulfenylated N-Boc-protected oxindoles.

8. Observation of direct sulfenium and selenenium group transfer from thiiranium and seleniranium ions to alkenes.

9. Chiral anion-mediated asymmetric ring opening of meso-aziridinium and episulfonium ions.

10. Catalytic Alkene Cyclization Reactions for the Stereoselective Synthesis of Complex "Terpenoid-like" Heterocycles.

1. (R)-N,N'-Dimethyl-1,1'-binaphthyldiamine.

2. Structural, Mechanistic, Spectroscopic, and Preparative Studies on the Lewis Base Catalyzed, Enantioselective Sulfenofunctionalization of Alkenes.

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

4. Enantio- and Diastereoselective, Lewis Base Catalyzed, Cascade Sulfenoacetalization of Alkenyl Aldehydes.

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

Review 6. Catalytic, Enantioselective Sulfenofunctionalization of Alkenes: Development and Recent Advances.

7. Metal-free Chlorothiolation of Alkenes using HCl and Sulfoxides.

8. Iron-catalyzed cross-coupling of unactivated secondary alkyl thio ethers and sulfones with aryl Grignard reagents.

9. Enantioselective, Lewis Base-Catalyzed Sulfenocyclization of Polyenes.

10. Investigating the Enantiodetermining Step of a Chiral Lewis Base Catalyzed Bromocycloetherification of Privileged Alkenes.