Literature DB >> 19902942

Palladium-catalyzed enantioselective addition of two distinct nucleophiles across alkenes capable of quinone methide formation.

Katrina H Jensen1, Tejas P Pathak, Yang Zhang, Matthew S Sigman.   

Abstract

A sequential intramolecular-intermolecular enantioselective alkene difunctionalization reaction has been developed which is thought to proceed through Pd-catalyzed quinone methide formation. The synthesis of new chiral heterocyclic compounds with adjacent chiral centers is achieved in enantiomeric ratios up to 99:1 and diastereomeric ratios up to 10:1.

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Year:  2009        PMID： 19902942      PMCID： PMC2792916          DOI： 10.1021/ja909030c

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


  21 in total

1.  Copper(II)-catalyzed enantioselective intramolecular carboamination of alkenes.

Authors:  Wei Zeng; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2007-10-05       Impact factor: 15.419

2.  Copper(II) acetate promoted intramolecular diamination of unactivated olefins.

Authors:  Thomas P Zabawa; Dhanalakshmi Kasi; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2005-08-17       Impact factor: 15.419

3.  Metal-catalysed 1,2-diamination reactions.

Authors:  Francesca Cardona; Andrea Goti
Journal:  Nat Chem       Date:  2009-06-22       Impact factor: 24.427

4.  Palladium(II)-catalyzed aerobic dialkoxylation of styrenes: a profound influence of an o-phenol.

Authors:  Mitchell J Schultz; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2006-02-08       Impact factor: 15.419

5.  Palladium-catalyzed diacetoxylation of alkenes with molecular oxygen as sole oxidant.

Authors:  Azhong Wang; Huanfeng Jiang; Huoji Chen
Journal:  J Am Chem Soc       Date:  2009-03-25       Impact factor: 15.419

6.  Copper catalyzed enantioselective intramolecular aminooxygenation of alkenes.

Authors:  Peter H Fuller; Jin-Woo Kim; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2008-12-31       Impact factor: 15.419

Review 7.  C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents.

Authors:  Egle M Beccalli; Gianluigi Broggini; Michela Martinelli; Silvia Sottocornola
Journal:  Chem Rev       Date:  2007-11-01       Impact factor: 60.622

8.  Anionic halocuprate(II) complexes as catalysts for the oxaziridine-mediated aminohydroxylation of olefins.

Authors:  Tamas Benkovics; Juana Du; Ilia A Guzei; Tehshik P Yoon
Journal:  J Org Chem       Date:  2009-08-07       Impact factor: 4.354

9.  Palladium-catalyzed carboamination of alkenes promoted by N-fluorobenzenesulfonimide via C-H activation of arenes.

Authors:  Carolyn F Rosewall; Paul A Sibbald; Dmitry V Liskin; Forrest E Michael
Journal:  J Am Chem Soc       Date:  2009-07-15       Impact factor: 15.419

10.  A direct route to fluostatin C by a fascinating Diels-Alder reaction.

Authors:  Maolin Yu; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2008-02-07       Impact factor: 15.419
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  27 in total

1.  Enantioselective synthesis of hindered cyclic dialkyl ethers via catalytic oxa-Michael/Michael desymmetrization.

Authors:  Michael T Corbett; Jeffrey S Johnson
Journal:  Chem Sci       Date:  2013-07-01       Impact factor: 9.825

2.  Mechanism and enantioselectivity in palladium-catalyzed conjugate addition of arylboronic acids to β-substituted cyclic enones: insights from computation and experiment.

Authors:  Jeffrey C Holder; Lufeng Zou; Alexander N Marziale; Peng Liu; Yu Lan; Michele Gatti; Kotaro Kikushima; K N Houk; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2013-09-27       Impact factor: 15.419

3.  Palladium(II)-catalyzed enantio- and diastereoselective synthesis of pyrrolidine derivatives.

Authors:  Ranjan Jana; Tejas P Pathak; Katrina H Jensen; Matthew S Sigman
Journal:  Org Lett       Date:  2012-08-08       Impact factor: 6.005

4.  Enantioselective Borylation of Aromatic C-H Bonds with Chiral Dinitrogen Ligands.

Authors:  Bo Su; Tai-Gang Zhou; Pei-Lin Xu; Zhang-Jie Shi; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-16       Impact factor: 15.336

5.  Pd(II)-catalyzed oxidative 1,1-diarylation of terminal olefins.

Authors:  Erik W Werner; Kaveri B Urkalan; Matthew S Sigman
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

6.  Synthesis and preliminary biological studies of 3-substituted indoles accessed by a palladium-catalyzed enantioselective alkene difunctionalization reaction.

Authors:  Tejas P Pathak; Keith M Gligorich; Bryan E Welm; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2010-06-16       Impact factor: 15.419

7.  A Chiral Nitrogen Ligand for Enantioselective, Iridium-Catalyzed Silylation of Aromatic C-H Bonds.

Authors:  Bo Su; Tai-Gang Zhou; Xian-Wei Li; Xiao-Ru Shao; Pei-Lin Xu; Wen-Lian Wu; John F Hartwig; Zhang-Jie Shi
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-15       Impact factor: 15.336

8.  Preparation of (S)-tert-ButylPyOx and Palladium-catalyzed Asymmetric Conjugate Addition of Arylboronic Acids.

Authors:  Jeffrey C Holder; Samantha E Shockley; Mario P Wiesenfeldt; Hideki Shimizu; Brian M Stoltz
Journal:  Organic Synth       Date:  2016-03-04

9.  Palladium-Catalyzed Enantioselective Intermolecular Coupling of Phenols and Allylic Alcohols.

Authors:  Nicholas J Race; Cristiane S Schwalm; Takayuki Nakamuro; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2016-12-01       Impact factor: 15.419

10.  Enantioselective Multicomponent Condensation Reactions of Phenols, Aldehydes, and Boronates Catalyzed by Chiral Biphenols.

Authors:  Keith S Barbato; Yi Luan; Daniele Ramella; James S Panek; Scott E Schaus
Journal:  Org Lett       Date:  2015-11-18       Impact factor: 6.005
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