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Literature DB >> 19434637

Cycle-specific organocascade catalysis: application to olefin hydroamination, hydro-oxidation, and amino-oxidation, and to natural product synthesis.

Bryon Simmons¹, Abbas M Walji, David W C MacMillan.

Abstract

United in effort: The combined application of iminium (Im) and enamine (En) catalysts can effect a range of valuable asymmetric transformations including 1,2-hydroamination, -hydro-oxidation, and -amino-oxidation of olefins (see picture). An enantioselective organocascade catalysis was also applied in the synthesis of a complex natural product.

Entities: Chemical Disease Species

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Year: 2009 PMID： 19434637 PMCID： PMC3057093 DOI： 10.1002/anie.200900220

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

25 in total

1. A facile and rapid route to highly enantiopure 1,2-diols by novel catalytic asymmetric alpha-aminoxylation of aldehydes.

Authors: Guofu Zhong
Journal: Angew Chem Int Ed Engl Date: 2003-09-15 Impact factor: 15.336

Review 2. Catalytic asymmetric tandem transformations triggered by conjugate additions.

Authors: Hong-Chao Guo; Jun-An Ma
Journal: Angew Chem Int Ed Engl Date: 2006-01-09 Impact factor: 15.336

Review 3. Asymmetric enamine catalysis.

Authors: Santanu Mukherjee; Jung Woon Yang; Sebastian Hoffmann; Benjamin List
Journal: Chem Rev Date: 2007-12 Impact factor: 60.622

Review 4. Hydroamination: direct addition of amines to alkenes and alkynes.

Authors: Thomas E Müller; Kai C Hultzsch; Miguel Yus; Francisco Foubelo; Mizuki Tada
Journal: Chem Rev Date: 2008-08-26 Impact factor: 60.622

5. Asymmetric multicomponent domino reactions and highly enantioselective conjugated addition of thiols to alpha,beta-unsaturated aldehydes.

Authors: Mauro Marigo; Tobias Schulte; Johan Franzén; Karl Anker Jørgensen
Journal: J Am Chem Soc Date: 2005-11-16 Impact factor: 15.419

6. Enantioselective organo-cascade catalysis.

Authors: Yong Huang; Abbas M Walji; Catharine H Larsen; David W C MacMillan
Journal: J Am Chem Soc Date: 2005-11-02 Impact factor: 15.419

7. Direct catalytic asymmetric alpha-amination of aldehydes.

Authors: Benjamin List
Journal: J Am Chem Soc Date: 2002-05-22 Impact factor: 15.419

8. The first enantioselective organocatalytic Mukaiyama-Michael reaction: a direct method for the synthesis of enantioenriched gamma-butenolide architecture.

Authors: Sean P Brown; Nicole C Goodwin; David W C MacMillan
Journal: J Am Chem Soc Date: 2003-02-05 Impact factor: 15.419

9. One-pot multi-component asymmetric cascade reactions catalyzed by soluble star polymers with highly branched non-interpenetrating catalytic cores.

Authors: Yonggui Chi; Steven T Scroggins; Jean M J Fréchet
Journal: J Am Chem Soc Date: 2008-04-24 Impact factor: 15.419

10. The direct and enantioselective organocatalytic alpha-oxidation of aldehydes.

Authors: Sean P Brown; Michael P Brochu; Christopher J Sinz; David W C MacMillan
Journal: J Am Chem Soc Date: 2003-09-10 Impact factor: 15.419

33 in total

1. Multicatalytic, asymmetric Michael/Stetter reaction of salicylaldehydes and activated alkynes.

Authors: Claire M Filloux; Stephen P Lathrop; Tomislav Rovis
Journal: Proc Natl Acad Sci U S A Date: 2010-07-16 Impact factor: 11.205

Review 2. Organocatalytic cascade reactions as a new tool in total synthesis.

Authors: Christoph Grondal; Matthieu Jeanty; Dieter Enders
Journal: Nat Chem Date: 2010-02-19 Impact factor: 24.427

3. Collective synthesis of natural products by means of organocascade catalysis.

Authors: Spencer B Jones; Bryon Simmons; Anthony Mastracchio; David W C MacMillan
Journal: Nature Date: 2011-07-13 Impact factor: 49.962

4. Natural product synthesis at the interface of chemistry and biology.

Authors: Jiyong Hong
Journal: Chemistry Date: 2014-07-10 Impact factor: 5.236

5. Stereodivergent Allylic Substitutions with Aryl Acetic Acid Esters by Synergistic Iridium and Lewis Base Catalysis.

Authors: Xingyu Jiang; Jason J Beiger; John F Hartwig
Journal: J Am Chem Soc Date: 2016-12-22 Impact factor: 15.419

6. Allylation of nitrosobenzene with pinacol allylboronates. A regioselective complement to peroxide oxidation.

Authors: Robert E Kyne; Michael C Ryan; Laura T Kliman; James P Morken
Journal: Org Lett Date: 2010-09-03 Impact factor: 6.005

7. Nine-step enantioselective total synthesis of (-)-vincorine.

Authors: Benjamin D Horning; David W C MacMillan
Journal: J Am Chem Soc Date: 2013-04-19 Impact factor: 15.419

8. Mechanistic analysis and optimization of the copper-catalyzed enantioselective intramolecular alkene aminooxygenation.

Authors: Monissa C Paderes; Jerome B Keister; Sherry R Chemler
Journal: J Org Chem Date: 2012-12-28 Impact factor: 4.354

9. Outer-Sphere Control for Divergent Multicatalysis with Common Catalytic Moieties.

Authors: Christopher R Shugrue; Bianca R Sculimbrene; Elizabeth R Jarvo; Brandon Q Mercado; Scott J Miller
Journal: J Org Chem Date: 2019-01-16 Impact factor: 4.354

10. Methods for direct alkene diamination, new & old.

Authors: Sam de Jong; Daniel G Nosal; Duncan J Wardrop
Journal: Tetrahedron Date: 2012-03-21 Impact factor: 2.457