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Literature DB >> 23244238

N-heterocyclic carbene-catalyzed Ireland-Coates Claisen rearrangement: synthesis of functionalized β-lactones.

Abstract

The N-heterocyclic carbene (NHC)-catalyzed Claisen rearrangement of hybrid Ireland-Coates structures has been achieved, allowing the stereoselective synthesis of highly functionalized β-lactones. The reaction proceeds with high diastereoselectivity (>20:1) and affords a diverse range of β-lactone fused cyclopentanes. Mechanistic studies are detailed.

Entities: Chemical Disease

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Year: 2012 PMID： 23244238 DOI： 10.1021/ja310449k

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

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Cited

10 in total

Review 1. Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

Authors: Darrin M Flanigan; Fedor Romanov-Michailidis; Nicholas A White; Tomislav Rovis
Journal: Chem Rev Date: 2015-05-20 Impact factor: 60.622

2. N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.

Authors: Anna Lee; Karl A Scheidt
Journal: Chem Commun (Camb) Date: 2015-02-25 Impact factor: 6.222

3. Catalytic Kinetic Resolution of a Dynamic Racemate: Highly Stereoselective β-Lactone Formation by N-Heterocyclic Carbene Catalysis.

Authors: Ryne C Johnston; Daniel T Cohen; Chad C Eichman; Karl A Scheidt; Paul Ha-Yeon Cheong
Journal: Chem Sci Date: 2014-05-01 Impact factor: 9.825

9. Highly enantioselective sulfa-Michael addition reactions using N-heterocyclic carbene as a non-covalent organocatalyst.

Authors: Jiean Chen; Sixuan Meng; Leming Wang; Hongmei Tang; Yong Huang
Journal: Chem Sci Date: 2015-04-23 Impact factor: 9.825

10. Enantioselective annulation of enals with 2-naphthols by triazolium salts derived from l-phenylalanine.

Authors: Guo-Tai Li; Qing Gu; Shu-Li You
Journal: Chem Sci Date: 2015-04-30 Impact factor: 9.825

10 in total

N-heterocyclic carbene-catalyzed Ireland-Coates Claisen rearrangement: synthesis of functionalized β-lactones.

Review 1. Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

2. N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.

3. Catalytic Kinetic Resolution of a Dynamic Racemate: Highly Stereoselective β-Lactone Formation by N-Heterocyclic Carbene Catalysis.

4. Rapid assembly of complex cyclopentanes employing chiral, α,β-unsaturated acylammonium intermediates.

5. NHC-Catalyzed Asymmetric Synthesis of Functionalized Succinimides from Enals and α-Ketoamides.

Review 6. N-Heterocyclic-Carbene-Catalyzed Domino Reactions via Two or More Activation Modes.

7. Desymmetrization of N-Cbz glutarimides through N-heterocyclic carbene organocatalysis.

8. Enantioselective annulations for dihydroquinolones by in situ generation of azolium enolates.

9. Highly enantioselective sulfa-Michael addition reactions using N-heterocyclic carbene as a non-covalent organocatalyst.

10. Enantioselective annulation of enals with 2-naphthols by triazolium salts derived from l-phenylalanine.