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Literature DB >> 12822967

Catalytic enone cycloallylation via concomitant activation of latent nucleophilic and electrophilic partners: merging organic and transition metal catalysis.

Bradley G Jellerichs¹, Jong-Rock Kong, Michael J Krische.

Abstract

Upon exposure of mono-enone mono-allylic carbonates to tributylphosphine and 1 mol % Pd(Ph3P)4, efficient conversion to the corresponding cycloallylated products is achieved. This transformation combines the nucleophilic features of the Morita-Baylis-Hillman reaction with the electrophilic features of the Trost-Tsuji reaction.

Entities: Chemical

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Year: 2003 PMID： 12822967 DOI： 10.1021/ja0301469

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

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Cited

10 in total

1. Direct Copper-Free Domino Conjugate Addition-Cycloallylation using Organozinc Reagents.

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3. De novo asymmetric synthesis of the mezzettiaside family of natural products via the iterative use of a dual B-/Pd-catalyzed glycosylation.

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4. Cu-catalyzed cross-dehydrogenative coupling: a versatile strategy for C-C bond formations via the oxidative activation of sp(3) C-H bonds.

Authors: Zhiping Li; D Scott Bohle; Chao-Jun Li
Journal: Proc Natl Acad Sci U S A Date: 2006-06-05 Impact factor: 11.205

5. Acyclic Quaternary Carbon Stereocenters via Enantioselective Transition Metal Catalysis.

Authors: Jiajie Feng; Michael Holmes; Michael J Krische
Journal: Chem Rev Date: 2017-09-14 Impact factor: 60.622

6. Concise stereocontrolled formal synthesis of (+/-)-quinine and total synthesis of (+/-)-7- hydroxyquinine via merged Morita-Baylis-Hillman-Tsuji-Trost cyclization.

Authors: Peter Webber; Michael J Krische
Journal: J Org Chem Date: 2008-12-05 Impact factor: 4.354

Catalytic enone cycloallylation via concomitant activation of latent nucleophilic and electrophilic partners: merging organic and transition metal catalysis.

1. Direct Copper-Free Domino Conjugate Addition-Cycloallylation using Organozinc Reagents.

2. A Cooperative N-Heterocyclic Carbene/Palladium Catalysis System.

3. De novo asymmetric synthesis of the mezzettiaside family of natural products via the iterative use of a dual B-/Pd-catalyzed glycosylation.

4. Cu-catalyzed cross-dehydrogenative coupling: a versatile strategy for C-C bond formations via the oxidative activation of sp(3) C-H bonds.

5. Acyclic Quaternary Carbon Stereocenters via Enantioselective Transition Metal Catalysis.

6. Concise stereocontrolled formal synthesis of (+/-)-quinine and total synthesis of (+/-)-7- hydroxyquinine via merged Morita-Baylis-Hillman-Tsuji-Trost cyclization.

7. Palladium-catalyzed synthesis of N-aryl carbamates.

8. Asymmetric total synthesis of the iridoid beta-glucoside (+)-geniposide via phosphine organocatalysis.

9. Stereodivergent Coupling of Aldehydes and Alkynes via Synergistic Catalysis Using Rh and Jacobsen's Amine.

Review 10. Review on Abyssomicins: Inhibitors of the Chorismate Pathway and Folate Biosynthesis.