Literature DB >> 19053737

Diastereoselective oxidative carbon-carbon bond formation via silyl bis-enol ethers.

Christopher T Avetta1, Leah C Konkol, Carla N Taylor, Karen C Dugan, Charlotte L Stern, Regan J Thomson.   

Abstract

Diisopropylsilyl bis-enol ethers are shown to be powerful intermediates for the diastereoselective dimerization and cross-coupling of cyclic ketones. The trends observed for the oxidative coupling of a range of different dialkylsilyl bis-enol ethers derived from cyclohexanone are rationalized by invoking a stereochemical model based on a Thorpe-Ingold effect.

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Year:  2008        PMID： 19053737     DOI： 10.1021/ol802516z

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


  11 in total

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2.  On the nature of the oxidative heterocoupling of lithium enolates.

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5.  Development of enantioselective synthetic routes to (-)-kinamycin F and (-)-lomaiviticin aglycon.

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Journal:  J Am Chem Soc       Date:  2012-10-03       Impact factor: 15.419

6.  Oxidative carbon-carbon bond formation via allyldimethylsilyl enol ethers.

Authors:  Leah C Konkol; Brian T Jones; Regan J Thomson
Journal:  Org Lett       Date:  2009-12-03       Impact factor: 6.005

7.  Oxidative Coupling of Enolates, Enol Silanes and Enamines: Methods and Natural Product Synthesis.

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8.  Development of a merged conjugate addition/oxidative coupling sequence. Application to the enantioselective total synthesis of metacycloprodigiosin and prodigiosin R1.

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Journal:  J Am Chem Soc       Date:  2009-10-14       Impact factor: 15.419

9.  Access to α-Pyrazole and α-Triazole Derivatives of Ketones from Oxidative Heteroarylation of Silyl Enolethers.

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10.  Total Synthesis of Propolisbenzofuran B.

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