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Literature DB >> 19905027

Chiral phosphoric acid-catalyzed desymmetrization of meso-aziridines with functionalized mercaptans.

Shawn E Larson¹, Juan C Baso, Guilong Li, Jon C Antilla.

Abstract

Conditions for the phosphoric acid-catalyzed highly enantioselective ring-opening of meso-aziridines with a series of functionalized aromatic thiol nucleophiles are described. The procedure utilizes commercially available aromatic thiols, a series of meso-aziridines, and a catalytic amount of VAPOL phosphoric acid to explore the substrate scope of this highly enantioselective reaction.

Entities: Chemical Disease Gene

Mesh：

Substances：

Year: 2009 PMID： 19905027 PMCID： PMC2780433 DOI： 10.1021/ol902123h

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

15 in total

1. Enantioselective ring opening of meso aziridines catalyzed by Tridentate Schiff base chromium(III) complexes.

Authors: Z Li; M Fernández; E N Jacobsen
Journal: Org Lett Date: 1999-11-18 Impact factor: 6.005

2. Chiral phosphoric acids: powerful organocatalysts for asymmetric addition reactions to imines.

Authors: Stephen J Connon
Journal: Angew Chem Int Ed Engl Date: 2006-06-12 Impact factor: 15.336

3. Chiral sulfur ligands for asymmetric catalysis.

Authors: Mohamed Mellah; Arnaud Voituriez; Emmanuelle Schulz
Journal: Chem Rev Date: 2007-10-18 Impact factor: 60.622

4. Binaphthol-derived phosphoric acid as a versatile catalyst for enantioselective carbon-carbon bond forming reactions.

Authors: Masahiro Terada
Journal: Chem Commun (Camb) Date: 2008-07-11 Impact factor: 6.222

5. Catalytic enantioselective desymmetrization of meso-N-acylaziridines with TMSCN.

Authors: Tsuyoshi Mita; Ikuo Fujimori; Reiko Wada; Jianfeng Wen; Motomu Kanai; Masakatsu Shibasaki
Journal: J Am Chem Soc Date: 2005-08-17 Impact factor: 15.419

6. Catalytic, enantioselective ring opening of aziridines.

Authors: Christoph Schneider
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

7. Brønsted acid-catalyzed desymmetrization of meso-aziridines.

Authors: Emily B Rowland; Gerald B Rowland; Edwin Rivera-Otero; Jon C Antilla
Journal: J Am Chem Soc Date: 2007-09-18 Impact factor: 15.419

8. VAPOL phosphoric acid catalysis: the highly enantioselective addition of imides to imines.

Authors: Yuxue Liang; Emily B Rowland; Gerald B Rowland; Jason A Perman; Jon C Antilla
Journal: Chem Commun (Camb) Date: 2007-08-21 Impact factor: 6.222

9. Catalytic asymmetric addition of alcohols to imines: enantioselective preparation of chiral N,O-aminals.

Authors: Guilong Li; Frank R Fronczek; Jon C Antilla
Journal: J Am Chem Soc Date: 2008-08-23 Impact factor: 15.419

10. Enantioselective desymmetrization of meso-aziridines with TMSN3 or TMSCN catalyzed by discrete yttrium complexes.

Authors: Bin Wu; Judith C Gallucci; Jon R Parquette; T V RajanBabu
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

6 in total

1. Vaulted biaryls in catalysis: A structure-activity relationship guided tour of the immanent domain of the VANOL ligand.

Authors: Yong Guan; Zhensheng Ding; William D Wulff
Journal: Chemistry Date: 2013-10-02 Impact factor: 5.236

2. Palladium-Catalyzed, Enantioselective Heine Reaction.

Authors: Molly Punk; Charlotte Merkley; Katlyn Kennedy; Jeremy B Morgan
Journal: ACS Catal Date: 2016-06-15 Impact factor: 13.084

3. Cooperative benzylic-oxyallylic stabilized cations: regioselective construction of α-quaternary centers in ketone-derived compounds.

Authors: Nitin S Dange; Jacob R Stepherson; Caitlan E Ayala; Frank R Fronczek; Rendy Kartika
Journal: Chem Sci Date: 2015-07-22 Impact factor: 9.825