Literature DB >> 16594693

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

Barry M Trost1, Yong Zhang.   

Abstract

The first example of Mo-catalyzed asymmetric allylation for the generation of quaternary stereocenters at a prochiral nucleophile is reported. A variety of 3-alkyl oxindoles can be alkylated with high yields and enantioselectivity. This method provides expedited access to (-)-physostigmine and its analogues.

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Year:  2006        PMID: 16594693     DOI: 10.1021/ja060560j

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


  27 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.  Deacylative allylation: allylic alkylation via retro-Claisen activation.

Authors:  Alexander J Grenning; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2011-08-24       Impact factor: 15.419

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

6.  Pardon the Interruption: A Modification of Fischer's Venerable Reaction for the Synthesis of Heterocycles and Natural Products.

Authors:  Robert B Susick; Lucas A Morrill; Elias Picazo; Neil K Garg
Journal:  Synlett       Date:  2017       Impact factor: 2.454

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

Authors:  Barry M Trost; Yong Zhang
Journal:  J Am Chem Soc       Date:  2007-11-07       Impact factor: 15.419

8.  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

9.  Recent developments in the catalytic, asymmetric construction of pyrroloindolines bearing all-carbon quaternary stereocenters.

Authors:  Lindsay M Repka; Sarah E Reisman
Journal:  J Org Chem       Date:  2013-12-02       Impact factor: 4.354

10.  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

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