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Literature DB >> 25169904

Catalyst-directed diastereo- and site-selectivity in successive nucleophilic and electrophilic allylations of chiral 1,3-diols: protecting-group-free synthesis of substituted pyrans.

Inji Shin¹, Gang Wang, Michael J Krische.

Abstract

The iridium-catalyzed, protecting group-free synthesis of 4-hydroxy-2,6-cis- or trans-pyrans through successive nucleophilic and electrophilic allylations of chiral 1,3-diols occurs with complete levels of catalyst-directed diastereoselectivity in the absence of protecting groups, premetallated reagents, or discrete alcohol-to-aldehyde redox reactions.

Entities: Chemical Gene Species

Keywords: catalyst-directed diastereoselectivity; polyketides; protecting group-free reactions; pyran; transfer hydrogenation

Mesh：

Substances：

Year: 2014 PMID： 25169904 PMCID： PMC4177504 DOI： 10.1002/chem.201404065

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

53 in total

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2. Mechanistically driven development of iridium catalysts for asymmetric allylic substitution.

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Journal: Acc Chem Res Date: 2010-09-28 Impact factor: 22.384

3. Synthesis of cardiac glycoside analogs by catalyst-controlled, regioselective glycosylation of digitoxin.

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Journal: Org Lett Date: 2013-03-06 Impact factor: 6.005

4. Unlocking Hydrogenation for C-C Bond Formation: A Brief Overview of Enantioselective Methods.

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Journal: Org Process Res Dev Date: 2011-11-18 Impact factor: 3.317

5. Regioselective alkylation of carbohydrate derivatives catalyzed by a diarylborinic acid derivative.

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Journal: Org Lett Date: 2011-05-17 Impact factor: 6.005

6. Catalytic site-selective synthesis and evaluation of a series of erythromycin analogs.

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7. Stereocontrolled access to isoprostanes via a bicyclo[3.3.0]octene framework.

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Journal: Org Lett Date: 2008-10-10 Impact factor: 6.005

8. Asymmetric catalysis at a distance: catalytic, site-selective phosphorylation of teicoplanin.

Authors: Sunkyu Han; Scott J Miller
Journal: J Am Chem Soc Date: 2013-08-07 Impact factor: 15.419

9. Chemical tailoring of teicoplanin with site-selective reactions.

Authors: Tejas P Pathak; Scott J Miller
Journal: J Am Chem Soc Date: 2013-05-21 Impact factor: 15.419

10. Catalyst-directed diastereoselectivity in hydrogenative couplings of acetylene to alpha-chiral aldehydes: formal synthesis of all eight L-hexoses.

Authors: Soo Bong Han; Jong Rock Kong; Michael J Krische
Journal: Org Lett Date: 2008-08-26 Impact factor: 6.005

24 in total

1. Total Synthesis of Swinholide A: An Exposition in Hydrogen-Mediated C-C Bond Formation.

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Journal: J Am Chem Soc Date: 2016-10-25 Impact factor: 15.419

Review 2. Asymmetric Iridium-Catalyzed C-C Coupling of Chiral Diols via Site-Selective Redox-Triggered Carbonyl Addition.

Authors: Inji Shin; Michael J Krische
Journal: Top Curr Chem Date: 2016

3. Successive Nucleophilic and Electrophilic Allylation for the Catalytic Enantioselective Synthesis of 2,4-Disubstituted Pyrrolidines.

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Journal: Org Lett Date: 2019-02-28 Impact factor: 6.005

4. Formal Synthesis of Premisakinolide A and C(19)-C(32) of Swinholide A via Site-Selective C-H Allylation and Crotylation of Unprotected Diols.

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Journal: Org Lett Date: 2015-10-02 Impact factor: 6.005

Review 5. Feedstock Reagents in Metal-Catalyzed Carbonyl Reductive Coupling: Minimizing Preactivation for Efficiency in Target-Oriented Synthesis.

Authors: Rosalie S Doerksen; Cole C Meyer; Michael J Krische
Journal: Angew Chem Int Ed Engl Date: 2019-07-26 Impact factor: 15.336

6. Diastereo- and Enantioselective Iridium Catalyzed Coupling of Vinyl Aziridines with Alcohols: Site-Selective Modification of Unprotected Diols and Synthesis of Substituted Piperidines.

Authors: Gang Wang; Jana Franke; Chinh Q Ngo; Michael J Krische
Journal: J Am Chem Soc Date: 2015-06-15 Impact factor: 15.419

7. Asymmetric Allylation of Glycidols Mediated by Allyl Acetate via Iridium-Catalyzed Hydrogen Transfer.

Authors: Seung Wook Kim; Wonchul Lee; Michael J Krische
Journal: Org Lett Date: 2017-02-21 Impact factor: 6.005

8. Hydroxymethylation beyond Carbonylation: Enantioselective Iridium-Catalyzed Reductive Coupling of Formaldehyde with Allylic Acetates via Enantiotopic π-Facial Discrimination.

Authors: Victoria J Garza; Michael J Krische
Journal: J Am Chem Soc Date: 2016-03-09 Impact factor: 15.419

9. Total Synthesis of (+)-SCH 351448: Efficiency via Chemoselectivity and Redox-Economy Powered by Metal Catalysis.

Authors: Gang Wang; Michael J Krische
Journal: J Am Chem Soc Date: 2016-06-23 Impact factor: 15.419

10. Diastereo- and Enantioselective Iridium Catalyzed Carbonyl (α-Cyclopropyl)allylation via Transfer Hydrogenation.

Authors: Ryosuke Tsutsumi; Suckchang Hong; Michael J Krische
Journal: Chemistry Date: 2015-07-28 Impact factor: 5.236