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Literature DB >> 19449882

Synthesis of 5,5-disubstituted butenolides based on a Pd-catalyzed gamma-arylation strategy.

Abstract

Methods for the construction of quaternary carbon centers are of great interest to synthetic chemists due to their presence in natural products. Development of the Pd-catalyzed arylation of butenolides with high selectivity for the gamma-position allows for a facile construction of quaternary centers. The preparation of a wide variety of gamma-aryl butenolides containing a number of functional groups is outlined. An application of this chemistry for a one-pot synthesis of a tricyclic tetrahydroisoquinolinone is demonstrated.

Entities: Chemical Disease Gene

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Year: 2009 PMID： 19449882 PMCID： PMC2739656 DOI： 10.1021/ol9007102

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

25 in total

1. Palladium-catalyzed alpha-arylation of esters and protected amino acids.

Authors: S Lee; N A Beare; J F Hartwig
Journal: J Am Chem Soc Date: 2001-08-29 Impact factor: 15.419

2. Palladium-catalyzed alpha-arylation of esters: ideal new methodology for discovery chemistry.

Authors: Guy C Lloyd-Jones
Journal: Angew Chem Int Ed Engl Date: 2002-03-15 Impact factor: 15.336

3. Catalytic use of selenium electrophiles in cyclizations.

Authors: Danielle M Browne; Osamu Niyomura; Thomas Wirth
Journal: Org Lett Date: 2007-07-04 Impact factor: 6.005

4. Palladium-catalyzed intramolecular alpha-arylation of alpha-amino acid esters.

Authors: Oliver Gaertzen; Stephen L Buchwald
Journal: J Org Chem Date: 2002-01-25 Impact factor: 4.354

5. Synthesis of alpha,beta-unsaturated 4,5-disubstituted gamma-lactones via ring-closing metathesis catalyzed by the first-generation Grubbs' catalyst.

Authors: Mauro Bassetti; Andrea D'Annibale; Alessia Fanfoni; Franco Minissi
Journal: Org Lett Date: 2005-04-28 Impact factor: 6.005

6. General approach for the synthesis of sarpagine/ajmaline indole alkaloids. Stereospecific total synthesis of the sarpagine alkaloid (+)-vellosimine.

Authors: T Wang; J M Cook
Journal: Org Lett Date: 2000-07-13 Impact factor: 6.005

Synthesis of 5,5-disubstituted butenolides based on a Pd-catalyzed gamma-arylation strategy.

1. Palladium-catalyzed alpha-arylation of esters and protected amino acids.

2. Palladium-catalyzed alpha-arylation of esters: ideal new methodology for discovery chemistry.

3. Catalytic use of selenium electrophiles in cyclizations.

4. Palladium-catalyzed intramolecular alpha-arylation of alpha-amino acid esters.

5. Synthesis of alpha,beta-unsaturated 4,5-disubstituted gamma-lactones via ring-closing metathesis catalyzed by the first-generation Grubbs' catalyst.

6. General approach for the synthesis of sarpagine/ajmaline indole alkaloids. Stereospecific total synthesis of the sarpagine alkaloid (+)-vellosimine.

7. Nickel-BINAP catalyzed enantioselective alpha-arylation of alpha-substituted gamma-butyrolactones.

8. Diastereoselective palladium-catalyzed alpha-arylation of 4-substituted cyclohexyl esters.

9. Alpha-arylation of esters catalyzed by the Pd(I) dimer {[P(t-Bu)3]PdBr}2.

10. Palladium-catalyzed alpha-arylation of esters with chloroarenes.

1. Palladium-catalyzed gamma-arylation of alpha,beta-unsaturated esters from silyl ketene acetals.