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Literature DB >> 17985899

Mo-catalyzed regio-, diastereo-, and enantioselective allylic alkylation of 3-aryloxindoles.

Abstract

A highly regio-, diastereo-, and enantioselective allylic alkylation reaction mediated by a chiral molybdenum catalyst has been developed as a novel entry into synthetically versatile 3-alkyl-3-aryloxindoles. Extremely bulky nucleophiles were employed to form a quaternary center and an adjacent tertiary center asymmetrically concurrently. The regio- and diastereoselectivity of the reaction is dependent upon the steric and electronic nature of the nucleophiles to an unusual degree. A reaction mechanism based on the bonding modes of molybdenum enolate complexes was discussed.

Entities: Chemical Disease

Mesh：

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Year: 2007 PMID： 17985899 PMCID： PMC2536500 DOI： 10.1021/ja0755717

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

16 in total

1. Mechanistic studies of the molybdenum-catalyzed asymmetric alkylation reaction.

Authors: David L Hughes; Guy C Lloyd-Jones; Shane W Krska; Laure Gouriou; Veronique D Bonnet; Kevin Jack; Yongkui Sun; David J Mathre; Robert A Reamer
Journal: Proc Natl Acad Sci U S A Date: 2004-03-31 Impact factor: 11.205

2. All-carbon quaternary stereogenic centers by enantioselective cu-catalyzed conjugate additions promoted by a chiral N-heterocyclic carbene.

Authors: M Kevin Brown; Tricia L May; Carl A Baxter; Amir H Hoveyda
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

3. Catalytic enantioselective synthesis of oxindoles and benzofuranones that bear a quaternary stereocenter.

Authors: Ivory D Hills; Gregory C Fu
Journal: Angew Chem Int Ed Engl Date: 2003-08-25 Impact factor: 15.336

4. Copper-catalyzed asymmetric conjugate addition of Grignard reagents to trisubstituted enones. Construction of all-carbon quaternary chiral centers.

Authors: David Martin; Stefan Kehrli; Magali d'Augustin; Hervé Clavier; Marc Mauduit; Alexandre Alexakis
Journal: J Am Chem Soc Date: 2006-07-05 Impact factor: 15.419

5. Molybdenum-catalyzed asymmetric allylation of 3-alkyloxindoles: application to the formal total synthesis of (-)-physostigmine.

Authors: Barry M Trost; Yong Zhang
Journal: J Am Chem Soc Date: 2006-04-12 Impact factor: 15.419

6. Cu-catalyzed asymmetric allylic alkylations of aromatic and aliphatic phosphates with alkylzinc reagents. An effective method for enantioselective synthesis of tertiary and quaternary carbons.

Authors: Monica A Kacprzynski; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2004-09-01 Impact factor: 15.419

7. Enantioselective total synthesis of quadrigemine C and psycholeine.

Authors: Alec D Lebsack; J T Link; Larry E Overman; Brian A Stearns
Journal: J Am Chem Soc Date: 2002-08-07 Impact factor: 15.419

8. Catalytic asymmetric synthesis of all-carbon quaternary stereocenters.

Authors: Christopher J Douglas; Larry E Overman
Journal: Proc Natl Acad Sci U S A Date: 2004-01-14 Impact factor: 11.205

9. Synthesis of novel quaternary amino acids using molybdenum-catalyzed asymmetric allylic alkylation.

Authors: Barry M Trost; Kalindi Dogra
Journal: J Am Chem Soc Date: 2002-06-26 Impact factor: 15.419

10. Synthesis and aldol reactivity of o- and C-enolate complexes of nickel.

Authors: Juan Cámpora; Celia M Maya; Pilar Palma; Ernesto Carmona; Enrique Gutiérrez-Puebla; Caridad Ruiz
Journal: J Am Chem Soc Date: 2003-02-12 Impact factor: 15.419

21 in total

1. The palladium catalyzed asymmetric addition of oxindoles and allenes: an atom-economical versatile method for the construction of chiral indole alkaloids.

Authors: Barry M Trost; Jia Xie; Joshua D Sieber
Journal: J Am Chem Soc Date: 2011-11-30 Impact factor: 15.419

2. Pd and Mo Catalyzed Asymmetric Allylic Alkylation.

Authors: Barry M Trost
Journal: Org Process Res Dev Date: 2012-01-13 Impact factor: 3.317

3. Alpha-arylation of 3-aryloxindoles.

Authors: Cheng-Kang Mai; Matthew F Sammons; Tarek Sammakia
Journal: Org Lett Date: 2010-05-21 Impact factor: 6.005

4. Development of the Regiodivergent Asymmetric Prenylation of 3-Substituted Oxindoles.

Authors: Barry M Trost; Walter H Chan; Sushant Malhotra
Journal: Chemistry Date: 2017-03-06 Impact factor: 5.236

5. Copper(II)- and palladium(II)-catalyzed enantioselective Claisen rearrangement of allyloxy- and propargyloxy-indoles to quaternary oxindoles and spirocyclic lactones.

Authors: Trung Cao; Elizabeth C Linton; Joshua Deitch; Simon Berritt; Marisa C Kozlowski
Journal: J Org Chem Date: 2012-12-04 Impact factor: 4.354

Review 6. Direct Asymmetric Alkylation of Ketones: Still Unconquered.

Authors: Rafael Cano; Armen Zakarian; Gerard P McGlacken
Journal: Angew Chem Int Ed Engl Date: 2017-06-27 Impact factor: 15.336

7. Catalytic double stereoinduction in asymmetric allylic alkylation of oxindoles.

Authors: Barry M Trost; Yong Zhang
Journal: Chemistry Date: 2010-01-04 Impact factor: 5.236

8. Cation control of diastereoselectivity in iridium-catalyzed allylic substitutions. Formation of enantioenriched tertiary alcohols and thioethers by allylation of 5H-oxazol-4-ones and 5H-thiazol-4-ones.

Authors: Wenyong Chen; John F Hartwig
Journal: J Am Chem Soc Date: 2013-12-19 Impact factor: 15.419

9. Palladium-catalyzed asymmetric allylic alkylation of 3-aryloxindoles with allylidene dipivalate: a useful enol pivalate product.

Authors: Barry M Trost; James T Masters; Aaron C Burns
Journal: Angew Chem Int Ed Engl Date: 2013-01-17 Impact factor: 15.336

10. AcOLeDMAP and BnOLeDMAP: conformationally restricted nucleophilic catalysts for enantioselective rearrangement of indolyl acetates and carbonates.

Authors: Trisha A Duffey; Scott A Shaw; Edwin Vedejs
Journal: J Am Chem Soc Date: 2009-01-14 Impact factor: 15.419