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Literature DB >> 20717504

Enantioselective α-Chlorination of Aldehydes with Recyclable Fluorous (S)-Pyrrolidine-Thiourea Bifunctional Organocatalyst.

Liang Wang¹, Chun Cai, Dennis P Curran, Wei Zhang.

Abstract

A novel fluorous (S)-pyrrolidine-thiourea bifunctional organocatalyst is prepared. The catalyst shows good activity and enantioselectivity for direct α-chlorination of aldehydes using N-chlorosuccinimide (NCS) as the chlorine source. It can be recovered from the reaction mixture by fluorous solid-phase extraction with excellent purity for direct reuse.

Entities: CellLine Chemical Disease

Year: 2010 PMID： 20717504 PMCID： PMC2922060 DOI： 10.1055/s-0029-1219198

Source DB: PubMed Journal: Synlett ISSN： 0936-5214 Impact factor: 2.454

15 in total

1. A Peptide/Oligourea/Azapeptide Hybrid That Adopts a Hairpin Turn.

Authors: Michael J. Soth; James S. Nowick
Journal: J Org Chem Date: 1999-01-08 Impact factor: 4.354

2. An efficient procedure for the preparation of (E)-alpha-alkylidenecycloalkanones mediated by a CeCl(3) x 7H(2)O-NaI system. Novel methodology for the synthesis of (S)-(-)-pulegone.

Authors: Giuseppe Bartoli; Marcella Bosco; Renato Dalpozzo; Arianna Giuliani; Enrico Marcantoni; Tiziana Mecozzi; Letizia Sambri; Elisabetta Torregiani
Journal: J Org Chem Date: 2002-12-13 Impact factor: 4.354

3. Catalytic enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes by using a simple thiourea organocatalyst.

Authors: Raquel P Herrera; Valentina Sgarzani; Luca Bernardi; Alfredo Ricci
Journal: Angew Chem Int Ed Engl Date: 2005-10-14 Impact factor: 15.336

4. A polymer-supported Cinchona-based bifunctional sulfonamide catalyst: a highly enantioselective, recyclable heterogeneous organocatalyst.

Authors: Sung Hun Youk; Sang Ho Oh; Ho Sik Rho; Je Eun Lee; Ji Woong Lee; Choong Eui Song
Journal: Chem Commun (Camb) Date: 2009-03-06 Impact factor: 6.222

5. Theoretical studies on the bifunctionality of chiral thiourea-based organocatalysts: competing routes to C-C bond formation.

Authors: Andrea Hamza; Gabor Schubert; Tibor Soós; Imre Papai
Journal: J Am Chem Soc Date: 2006-10-11 Impact factor: 15.419

6. A recyclable fluorous organocatalyst for Diels-Alder reactions.

Authors: Qianli Chu; Wei Zhang; Dennis P Curran
Journal: Tetrahedron Lett Date: 2006-12-25 Impact factor: 2.415

7. Direct organocatalytic asymmetric alpha-chlorination of aldehydes.

Authors: Nis Halland; Alan Braunton; Stephan Bachmann; Mauro Marigo; Karl Anker Jørgensen
Journal: J Am Chem Soc Date: 2004-04-21 Impact factor: 15.419

8. Enantioselectively organocatalytic Michael addition of ketones to alkylidene malonates.

Authors: Chun-Li Cao; Xiu-Li Sun; Jiao-Long Zhou; Yong Tang
Journal: J Org Chem Date: 2007-05-03 Impact factor: 4.354

9. Highly enantioselective desymmetrization of meso anhydrides by a bifunctional thiourea-based organocatalyst at low catalyst loadings and room temperature.

Authors: Aldo Peschiulli; Yurii Gun'ko; Stephen J Connon
Journal: J Org Chem Date: 2008-02-15 Impact factor: 4.354

5. Synthesis and properties of chiral thioureas bearing an additional function at a remote position tethered by a 1,5-disubstituted triazole.

Authors: Kiyosei Takasu; Takumi Azuma; Iderbat Enkhtaivan; Yoshiji Takemoto
Journal: Molecules Date: 2010-11-15 Impact factor: 4.411

5 in total

Enantioselective α-Chlorination of Aldehydes with Recyclable Fluorous (S)-Pyrrolidine-Thiourea Bifunctional Organocatalyst.

1. A Peptide/Oligourea/Azapeptide Hybrid That Adopts a Hairpin Turn.

2. An efficient procedure for the preparation of (E)-alpha-alkylidenecycloalkanones mediated by a CeCl(3) x 7H(2)O-NaI system. Novel methodology for the synthesis of (S)-(-)-pulegone.

3. Catalytic enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes by using a simple thiourea organocatalyst.

4. A polymer-supported Cinchona-based bifunctional sulfonamide catalyst: a highly enantioselective, recyclable heterogeneous organocatalyst.

5. Theoretical studies on the bifunctionality of chiral thiourea-based organocatalysts: competing routes to C-C bond formation.

6. A recyclable fluorous organocatalyst for Diels-Alder reactions.

7. Direct organocatalytic asymmetric alpha-chlorination of aldehydes.

8. Enantioselectively organocatalytic Michael addition of ketones to alkylidene malonates.

9. Highly enantioselective desymmetrization of meso anhydrides by a bifunctional thiourea-based organocatalyst at low catalyst loadings and room temperature.

10. Direct and enantioselective organocatalytic alpha-chlorination of aldehydes.

1. Rapid, one-pot synthesis of β-siloxy-α-haloaldehydes.

Review 2. Transition metal-free one-pot synthesis of nitrogen-containing heterocycles.

3. Recyclable fluorous cinchona alkaloid ester as a chiral promoter for asymmetric fluorination of β-ketoesters.

4. Enantioselective synthesis of tertiary α-chloro esters by non-covalent catalysis.

5. Synthesis and properties of chiral thioureas bearing an additional function at a remote position tethered by a 1,5-disubstituted triazole.