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Literature DB >> 15957939

Stereoselective conjugate radical additions: application of a fluorous oxazolidinone chiral auxiliary for efficient tin removal.

Jason E Hein¹, Jake Zimmerman, Mukund P Sibi, Philip G Hultin.

Abstract

[reaction: see text] A series of asymmetric free-radical-mediated intermolecular conjugate additions using a fluorous oxazolidinone chiral auxiliary has been completed. The fluorous auxiliary facilitated product isolation using fluorous solid phase extractions (FSPE), effectively removing excess organic and organometallic reagents. Parallel reactions carried out with a similar but nonfluorous norephedrine-derived oxazolidinone demonstrated the superior stereoselectivity and purification obtainable with the fluorous chiral auxiliary.

Entities: Chemical

Mesh：

Substances：

Year: 2005 PMID： 15957939 PMCID： PMC1524859 DOI： 10.1021/ol050956k

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

11 in total

1. Free radical reactions on soluble supports from ring-opening metathesis.

Authors: E J Enholm; M E Gallagher
Journal: Org Lett Date: 2001-10-18 Impact factor: 6.005

2. Construction of quaternary stereocenters: new perspectives through enantioselective Michael reactions.

Authors: Jens Christoffers; Angelika Baro
Journal: Angew Chem Int Ed Engl Date: 2003-04-17 Impact factor: 15.336

3. Stereoselective radical reactions.

Authors: Gregory Bar; Andrew F Parsons
Journal: Chem Soc Rev Date: 2003-09 Impact factor: 54.564

4. Enantioselective radical processes.

Authors: Mukund P Sibi; Shankar Manyem; Jake Zimmerman
Journal: Chem Rev Date: 2003-08 Impact factor: 60.622

5. Enantioselective radical addition/trapping reactions with alpha,beta-disubstituted unsaturated imides. Synthesis of anti-propionate aldols.

Authors: Mukund P Sibi; Goran Petrovic; Jake Zimmerman
Journal: J Am Chem Soc Date: 2005-03-02 Impact factor: 15.419

6. Stereocontrol in solid-phase radical reactions: radical addition to oxime ether anchored to polymer support

Authors:
Journal: Org Lett Date: 2000-05-18 Impact factor: 6.005

7. Free-radical-mediated conjugate additions. Enantioselective synthesis of butyrolactone natural products: (-)-enterolactone, (-)-arctigenin, (-)-isoarctigenin, (-)-nephrosteranic acid, and (-)-roccellaric acid.

Authors: Mukund P Sibi; Pingrong Liu; Jianguo Ji; Saumen Hajra; Jian-xie Chen
Journal: J Org Chem Date: 2002-03-22 Impact factor: 4.354

Stereoselective conjugate radical additions: application of a fluorous oxazolidinone chiral auxiliary for efficient tin removal.

1. Free radical reactions on soluble supports from ring-opening metathesis.

2. Construction of quaternary stereocenters: new perspectives through enantioselective Michael reactions.

3. Stereoselective radical reactions.

4. Enantioselective radical processes.

5. Enantioselective radical addition/trapping reactions with alpha,beta-disubstituted unsaturated imides. Synthesis of anti-propionate aldols.

6. Stereocontrol in solid-phase radical reactions: radical addition to oxime ether anchored to polymer support

7. Free-radical-mediated conjugate additions. Enantioselective synthesis of butyrolactone natural products: (-)-enterolactone, (-)-arctigenin, (-)-isoarctigenin, (-)-nephrosteranic acid, and (-)-roccellaric acid.

8. Silylated cyclohexadienes as new radical chain reducing reagents: preparative and mechanistic aspects.

9. KF-Silica as a stationary phase for the chromatographic removal of tin residues from organic compounds.

10. Lanthanide Lewis acid-mediated enantioselective conjugate radical additions.

1. Synthetic applications of fluorous solid-phase extraction (F-SPE).