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Literature DB >> 21711005

Regiodivergent reactions through catalytic enantioselective silylation of chiral diols. Synthesis of sapinofuranone A.

Jason M Rodrigo¹, Yu Zhao, Amir H Hoveyda, Marc L Snapper.

Abstract

Through the use of an amino acid based imidazole catalyst, a regiodivergent silylation of chiral diols in cases where there is not a significant steric and electronic difference between the regioisotopic hydroxyl groups has been developed. This transformation allows for the conversion of racemic diols into regioisomeric, enantiomerically enriched, monosilylated products. The utility of this process is highlighted in the efficient enantioselective preparation of a useful synthetic intermediate and the natural product, sapinofuranone A.

Entities: Chemical Species

Mesh：

Substances：
Furans
sapinofuranone A

Year: 2011 PMID： 21711005 PMCID： PMC3146572 DOI： 10.1021/ol2010819

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

13 in total

1. How Long Have Nonlinear Effects Been Known in the Field of Catalysis?

Authors:
Journal: Angew Chem Int Ed Engl Date: 2000-02 Impact factor: 15.336

2. Catalytic enantioselective radical cyclization via regiodivergent epoxide opening.

Authors: Andreas Gansäuer; Lei Shi; Matthias Otte
Journal: J Am Chem Soc Date: 2010-09-01 Impact factor: 15.419

3. Efficiency in nonenzymatic kinetic resolution.

Authors: Edwin Vedejs; Mara Jure
Journal: Angew Chem Int Ed Engl Date: 2005-06-27 Impact factor: 15.336

4. Total synthesis of kinamycins C, F, and J.

Authors: K C Nicolaou; Hongming Li; Andrea L Nold; Doron Pappo; Achim Lenzen
Journal: J Am Chem Soc Date: 2007-08-04 Impact factor: 15.419

5. Kinetic resolution of 1,2-diols through highly site- and enantioselective catalytic silylation.

Authors: Yu Zhao; Aurpon W Mitra; Amir H Hoveyda; Marc L Snapper
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

6. Titanocene-catalyzed regiodivergent epoxide openings.

Authors: Andreas Gansäuer; Chun-An Fan; Florian Keller; Jutta Keil
Journal: J Am Chem Soc Date: 2007-03-07 Impact factor: 15.419

7. Regiodivergent ring opening of chiral aziridines.

Authors: Bin Wu; Jon R Parquette; T V RajanBabu
Journal: Science Date: 2009-12-18 Impact factor: 47.728

8. Catalytic asymmetric Si-O coupling of simple achiral silanes and chiral donor-functionalized alcohols.

Authors: Andreas Weickgenannt; Marius Mewald; Thomas W T Muesmann; Martin Oestreich
Journal: Angew Chem Int Ed Engl Date: 2010-03-15 Impact factor: 15.336

9. Enantioselective silyl protection of alcohols catalysed by an amino-acid-based small molecule.

Authors: Yu Zhao; Jason Rodrigo; Amir H Hoveyda; Marc L Snapper
Journal: Nature Date: 2006-09-07 Impact factor: 49.962

10. Parallel kinetic resolution approach to the cyathane and cyanthiwigin diterpenes using a cyclopropanation/Cope rearrangement.

Authors: Laura C Miller; J Maina Ndungu; Richmond Sarpong
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

12 in total

Regiodivergent reactions through catalytic enantioselective silylation of chiral diols. Synthesis of sapinofuranone A.

1. How Long Have Nonlinear Effects Been Known in the Field of Catalysis?

2. Catalytic enantioselective radical cyclization via regiodivergent epoxide opening.

3. Efficiency in nonenzymatic kinetic resolution.

4. Total synthesis of kinamycins C, F, and J.

5. Kinetic resolution of 1,2-diols through highly site- and enantioselective catalytic silylation.

6. Titanocene-catalyzed regiodivergent epoxide openings.

7. Regiodivergent ring opening of chiral aziridines.

8. Catalytic asymmetric Si-O coupling of simple achiral silanes and chiral donor-functionalized alcohols.

9. Enantioselective silyl protection of alcohols catalysed by an amino-acid-based small molecule.

10. Parallel kinetic resolution approach to the cyathane and cyanthiwigin diterpenes using a cyclopropanation/Cope rearrangement.

1. Practical silyl protection of ribonucleosides.

2. Scaffolding Catalysis: Expanding the Repertoire of Bifunctional Catalysts.

3. Site-selective catalysis: toward a regiodivergent resolution of 1,2-diols.

Review 4. Synthesis of 5'-O-DMT-2'-O-TBS Mononucleosides Using an Organic Catalyst.

5. Resolution of terminal 1,2-diols via silyl transfer.

6. The efficient desymmetrization of glycerol using scaffolding catalysis.

7. Catalyst recognition of cis-1,2-diols enables site-selective functionalization of complex molecules.

8. Enantioselective silyl protection of alcohols promoted by a combination of chiral and achiral Lewis basic catalysts.

9. Enantioselective acyl transfer catalysis by a combination of common catalytic motifs and electrostatic interactions.

10. Broad-spectrum kinetic resolution of alcohols enabled by Cu-H-catalysed dehydrogenative coupling with hydrosilanes.