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Literature DB >> 20712333

Diastereoselective synthesis of 6-trifluoromethyl-5,6-dihydropyrans via phosphine-catalyzed [4 + 2] annulation of α-benzylallenoates with ketones.

Abstract

The highly diastereoselective synthesis of 6-trifluoromethyl-5,6-dihydropyrans was realized by the phosphine-catalyzed [4 + 2] annulation of ethyl α-benzylallenoates and trifluoromethyl ketones.

Entities: Chemical

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Year: 2010 PMID： 20712333 DOI： 10.1021/ol101762z

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

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Cited

11 in total

1. Phosphine-initiated general base catalysis: facile access to benzannulated 1,3-diheteroatom five-membered rings via double-Michael reactions of allenes.

Authors: Judy Szeto; Vardhineedi Sriramurthy; Ohyun Kwon
Journal: Org Lett Date: 2011-09-20 Impact factor: 6.005

2. Phosphine-catalyzed β'-umpolung addition of nucleophiles to activated α-alkyl allenes.

Authors: Tioga J Martin; Venus G Vakhshori; Yang S Tran; Ohyun Kwon
Journal: Org Lett Date: 2011-04-14 Impact factor: 6.005

3. Phosphine-catalyzed [4+2] annulations of 2-alkylallenoates and olefins: synthesis of multisubstituted cyclohexenes.

Authors: Yang S Tran; Tioga J Martin; Ohyun Kwon
Journal: Chem Asian J Date: 2011-07-07

Review 4. Phosphine Organocatalysis.

Authors: Hongchao Guo; Yi Chiao Fan; Zhanhu Sun; Yang Wu; Ohyun Kwon
Journal: Chem Rev Date: 2018-09-27 Impact factor: 60.622

10. Enantioselective [3 + 2] annulation of α-substituted allenoates with β,γ-unsaturated N-sulfonylimines catalyzed by a bifunctional dipeptide phosphine.

Authors: Huanzhen Ni; Weijun Yao; Yixin Lu
Journal: Beilstein J Org Chem Date: 2016-02-24 Impact factor: 2.883

Diastereoselective synthesis of 6-trifluoromethyl-5,6-dihydropyrans via phosphine-catalyzed [4 + 2] annulation of α-benzylallenoates with ketones.

1. Phosphine-initiated general base catalysis: facile access to benzannulated 1,3-diheteroatom five-membered rings via double-Michael reactions of allenes.

2. Phosphine-catalyzed β'-umpolung addition of nucleophiles to activated α-alkyl allenes.

3. Phosphine-catalyzed [4+2] annulations of 2-alkylallenoates and olefins: synthesis of multisubstituted cyclohexenes.

Review 4. Phosphine Organocatalysis.

5. Phosphine-Catalyzed Intramolecular Cyclizations of α-Nitroethylallenoates Forming (Z)-Furanone Oximes.

6. PHOSPHINE-CATALYZED [3 + 2] ANNULATION: SYNTHESIS OF ETHYL 5-(tert-BUTYL)-2-PHENYL-1-TOSYL-3-PYRROLINE-3-CARBOXYLATE.

7. Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs.

Review 8. Phosphine catalysis of allenes with electrophiles.

Review 9. Organophosphine-Catalyzed [4C+X] Annulations.

10. Enantioselective [3 + 2] annulation of α-substituted allenoates with β,γ-unsaturated N-sulfonylimines catalyzed by a bifunctional dipeptide phosphine.