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Literature DB >> 17705396

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

Abstract

The concept of Lewis base activation of Lewis acids has been applied to the selenolactonization reaction. Through the use of substoichiometric amounts of Lewis bases with "soft" donor atoms (S, Se, P) significant rate enhancements over the background reaction are seen. Preliminary mechanistic investigations have revealed the resting state of the catalyst as well as the significance of a weak Brønsted acid promoter.

Entities: Chemical Species

Mesh：

Substances：

Year: 2007 PMID： 17705396 DOI： 10.1021/ol701617d

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

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Cited

14 in total

1. 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

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

3. Reaction mechanism of organoselenium-catalyzed syn-dichlorination of alkenes: a DFT study.

Authors: Lijun Fu; Xueli Mu; Baiqing Li
Journal: J Mol Model Date: 2018-03-13 Impact factor: 1.810

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. Mechanistic, crystallographic, and computational studies on the catalytic, enantioselective sulfenofunctionalization of alkenes.

Authors: Scott E Denmark; Eduard Hartmann; David J P Kornfilt; Hao Wang
Journal: Nat Chem Date: 2014-11-10 Impact factor: 24.427

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

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

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

3. Reaction mechanism of organoselenium-catalyzed syn-dichlorination of alkenes: a DFT study.

4. Catalytic asymmetric thiofunctionalization of unactivated alkenes.

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

6. Mechanistic, crystallographic, and computational studies on the catalytic, enantioselective sulfenofunctionalization of alkenes.

7. Catalytic, enantioselective, intramolecular carbosulfenylation of olefins. Preparative and stereochemical aspects.

8. Catalytic, enantioselective, intramolecular carbosulfenylation of olefins.

9. Lewis Base Activation of Lewis Acids - Group 13. In Situ Generation and Reaction of Borenium Ions.

10. Seleniranium ion-triggered reactions: new aspects of Friedel-Crafts and N-detosylative cyclizations.