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Literature DB >> 19526479

Enantioselective linchpin catalysis by SOMO catalysis: an approach to the asymmetric alpha-chlorination of aldehydes and terminal epoxide formation.

Muriel Amatore¹, Teresa D Beeson, Sean P Brown, David W C MacMillan.

Abstract

Time for SOme MOre: For the first time SOMO (singly occupied molecular orbital) activation has been exploited to allow a new approach to the alpha-chlorination of aldehydes. This transformation can be readily implemented as part of a linchpin catalysis approach to the enantioselective production of terminal epoxides.

Entities: Chemical Disease Gene

Mesh：

Substances：
Aldehydes
Epoxy Compounds

Year: 2009 PMID： 19526479 PMCID： PMC3439133 DOI： 10.1002/anie.200901855

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

23 in total

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3. Strategies for catalytic asymmetric electrophilic alpha halogenation of carbonyl compounds.

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4. Catalytic asymmetric synthesis of tertiary alkyl chlorides.

Authors: Elaine C Lee; Kevin M McCauley; Gregory C Fu
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

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Journal: J Am Chem Soc Date: 2007-05-12 Impact factor: 15.419

Review 6. Asymmetric enamine catalysis.

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8. Designing new chiral ketone catalysts. Asymmetric epoxidation of cis-olefins and terminal olefins.

Authors: Hongqi Tian; Xuegong She; Hongwu Yu; Lianhe Shu; Yian Shi
Journal: J Org Chem Date: 2002-04-19 Impact factor: 4.354

9. Enantioselective organo-singly occupied molecular orbital catalysis: the carbo-oxidation of styrenes.

Authors: Thomas H Graham; Casey M Jones; Nathan T Jui; David W C MacMillan
Journal: J Am Chem Soc Date: 2008-12-10 Impact factor: 15.419

Review 10. Catalytic enantioselective diboration, disilation and silaboration: new opportunities for asymmetric synthesis.

Authors: Heather E Burks; James P Morken
Journal: Chem Commun (Camb) Date: 2007-08-22 Impact factor: 6.222

20 in total

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Journal: Proc Natl Acad Sci U S A Date: 2010-10-04 Impact factor: 11.205

2. A general approach to the enantioselective α-oxidation of aldehydes via synergistic catalysis.

Authors: Scott P Simonovich; Jeffrey F Van Humbeck; David W C Macmillan
Journal: Chem Sci Date: 2012 Impact factor: 9.825

3. Enantioselective polyene cyclization via organo-SOMO catalysis.

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Journal: J Am Chem Soc Date: 2010-04-14 Impact factor: 15.419

4. Enantioselective intramolecular aldehyde α-alkylation with simple olefins: direct access to homo-ene products.

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Journal: J Am Chem Soc Date: 2013-06-12 Impact factor: 15.419

5. Rapid, one-pot synthesis of β-siloxy-α-haloaldehydes.

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6. Asymmetric N-Heterocyclic Carbene (NHC) Catalyzed Acyl Anion Reactivity.

Authors: Harit U Vora; Tomislav Rovis
Journal: Aldrichimica Acta Date: 2011 Impact factor: 3.667

7. Chiral calcium VAPOL phosphate mediated asymmetric chlorination and Michael reactions of 3-substituted oxindoles.

Authors: Wenhua Zheng; Zuhui Zhang; Matthew J Kaplan; Jon C Antilla
Journal: J Am Chem Soc Date: 2011-02-22 Impact factor: 15.419

8. Norbornane-based cationic antimicrobial peptidomimetics targeting the bacterial membrane.

Authors: Shane M Hickey; Trent D Ashton; Gareth Boer; Christie A Bader; Michael Thomas; Alysha G Elliott; Carsten Schmuck; Heidi Y Yu; Jian Li; Roger L Nation; Matthew A Cooper; Sally E Plush; Douglas A Brooks; Frederick M Pfeffer
Journal: Eur J Med Chem Date: 2018-10-03 Impact factor: 6.514

9. Diasteroselective preparation of cyclopropanols using methylene bis(iodozinc).

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Journal: Org Lett Date: 2011-04-04 Impact factor: 6.005

10. N-Heterocyclic carbene catalyzed asymmetric hydration: direct synthesis of alpha-protio and alpha-deuterio alpha-chloro and alpha-fluoro carboxylic acids.

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Journal: J Am Chem Soc Date: 2010-03-10 Impact factor: 15.419