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Literature DB >> 16492030

Palladium-catalyzed chemo- and enantioselective oxidation of allylic esters and carbonates.

Barry M Trost¹, Jeffery Richardson, Kelvin Yong.

Abstract

The palladium-catalyzed oxidation of allylic esters and carbonates using a novel potassium nitronate has been developed. This method is highly chemoselective, leaving other esters, alcohols, thioethers, and amines undisturbed. The oxidation can be operated in two modes: an achiral mode, using either PPh3 or rac-2 as ligand, or a chiral and highly enantioselective mode, using 2 as ligand. The oxidative enantioselective desymmetrization of meso bis-esters provides a significantly shorter method to arrive at commonly used synthetic intermediates compared to other strategies. Highly efficient kinetic resolution is also possible using this methodology.

Entities: Chemical Gene

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Year: 2006 PMID： 16492030 PMCID： PMC2531164 DOI： 10.1021/ja057163d

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

5 in total

1. Asymmetric Alkylation of Nitroalkanes We thank the National Science Foundation and the National Institutes of Health (NIH), General Medical Sciences, for their generous support of our programs. Rhône-Poulenc graciously provided a postdoctoral fellowship for J.-P. S. Mass spectra were provided by the Mass Spectrometry Facility of the University of California, San Francisco, supported by the NIH Division of Research Resources.

Authors:
Journal: Angew Chem Int Ed Engl Date: 2000-09-01 Impact factor: 15.336

2. Synthetic studies toward the construction of the cis-decalin portion of superstolides A and B. Application of a sequential double michael reaction and an anionic oxy-Cope rearrangement.

Authors: Zhengmao Hua; Wensheng Yu; Mei Su; Zhendong Jin
Journal: Org Lett Date: 2005-05-12 Impact factor: 6.005

Palladium-catalyzed chemo- and enantioselective oxidation of allylic esters and carbonates.

2. Synthetic studies toward the construction of the cis-decalin portion of superstolides A and B. Application of a sequential double michael reaction and an anionic oxy-Cope rearrangement.

3. An enantioselective route to paeonilactone A via palladium- and copper-catalyzed reactions.

4. Studies towards the total synthesis of an epoxy isoprostane phospholipid, a potent activator of endothelial cells.

5. Asymmetric allylic alkylation, an enabling methodology.

1. Pd and Mo Catalyzed Asymmetric Allylic Alkylation.

Review 2. If C-H bonds could talk: selective C-H bond oxidation.

3. Metal Catalyzed Allylic Alkylation: Its Development in the Trost Laboratories.

4. A Highly Convergent Total Synthesis of Leustroducsin B.

5. Asymmetric synthesis of chiral cycloalkenone derivatives via palladium catalysis.