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Literature DB >> 15330612

Chiral benzyl centers through asymmetric catalysis. a three-step synthesis of (R)-(-)-alpha-curcumene via asymmetric hydrovinylation.

Abstract

[reaction: see text] A three-step, two-pot procedure involving asymmetric hydrovinylation followed by Suzuki-Miyaura reaction represents by far the shortest synthesis of this popular bisabolane. Other applications for the synthesis of similar compounds with chiral benzyl centers can be easily envisioned.

Entities: Chemical Disease

Mesh：

Substances：

Year: 2004 PMID： 15330612 DOI： 10.1021/ol048790v

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

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Cited

7 in total

1. Triarylphosphine Ligands with Hemilabile Alkoxy Groups. Ligands for Nickel(II)-Catalyzed Olefin Dimerization Reactions. Hydrovinylation of Vi-nylarenes, 1,3-Dienes, and Cycloisomerization of 1,6-Dienes.

Authors: Souvagya Biswas; Aibin Zhang; Balaram Raya; T V RajanBabu
Journal: Adv Synth Catal Date: 2014-07-01 Impact factor: 5.837

2. Ethylene in organic synthesis. Repetitive hydrovinylation of alkenes for highly enantioselective syntheses of pseudopterosins.

Authors: Daniel J Mans; G Adam Cox; T V RajanBabu
Journal: J Am Chem Soc Date: 2011-03-30 Impact factor: 15.419

3. In Pursuit of an Ideal C-C Bond-Forming Reaction: Development and Applications of the Hydrovinylation of Olefins.

Authors: T V Rajanbabu
Journal: Synlett Date: 2009 Impact factor: 2.454

4. Tunable Phosphoramidite Ligands for Asymmetric Hydrovinylation: Ligands par excellence for Generation of All-Carbon Quaternary Centers.

Authors: Craig R Smith; Hwan Jung Lim; Aibin Zhang; T V Rajanbabu
Journal: Synthesis (Stuttg) Date: 2009-01-01 Impact factor: 3.157

Chiral benzyl centers through asymmetric catalysis. a three-step synthesis of (R)-(-)-alpha-curcumene via asymmetric hydrovinylation.

1. Triarylphosphine Ligands with Hemilabile Alkoxy Groups. Ligands for Nickel(II)-Catalyzed Olefin Dimerization Reactions. Hydrovinylation of Vi-nylarenes, 1,3-Dienes, and Cycloisomerization of 1,6-Dienes.

2. Ethylene in organic synthesis. Repetitive hydrovinylation of alkenes for highly enantioselective syntheses of pseudopterosins.

3. In Pursuit of an Ideal C-C Bond-Forming Reaction: Development and Applications of the Hydrovinylation of Olefins.

4. Tunable Phosphoramidite Ligands for Asymmetric Hydrovinylation: Ligands par excellence for Generation of All-Carbon Quaternary Centers.

5. Selective [1,4]-Hydrovinylation of 1,3-Dienes with Unactivated Olefins Enabled by Iron Diimine Catalysts.

6. A short synthesis of bisabolane sesquiterpenes.

7. Tandem Peterson olefination and chemoselective asymmetric hydrogenation of β-hydroxy silanes.