Literature DB >> 21827171

Chemo- and regioselectivity-tunable Pd-catalyzed allylic alkylation of imines.

Jian-Ping Chen1, Qian Peng, Bai-Lin Lei, Xue-Long Hou, Yun-Dong Wu.   

Abstract

α-Carbanions of cyclic and acyclic imines have been successfully applied as nucleophiles in the Pd-catalyzed allylic alkylation reaction. Tuning of chemo- and regioselectivity has been realized by using t-BuOK/THF and LDA/toluene to give branched and linear products, respectively, with high regio- and diastereoselectivities. A plausible mechanism is proposed on the basis of the experimental results and DFT calculations.

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Year:  2011        PMID： 21827171     DOI： 10.1021/ja2039503

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


  13 in total

1.  Regio- and Enantioselective Iridium-Catalyzed N-Allylation of Indoles and Related Azoles with Racemic Branched Alkyl-Substituted Allylic Acetates.

Authors:  Seung Wook Kim; Tabitha T Schempp; Jason R Zbieg; Craig E Stivala; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-05-06       Impact factor: 15.336

2.  Metal-catalyzed Decarboxylative Fluoroalkylation Reactions.

Authors:  Brett R Ambler; Ming-Hsiu Yang; Ryan A Altman
Journal:  Synlett       Date:  2016-12       Impact factor: 2.454

3.  Regio- and Enantioselective Iridium-Catalyzed Amination of Racemic Branched Alkyl-Substituted Allylic Acetates with Primary and Secondary Aromatic and Heteroaromatic Amines.

Authors:  Seung Wook Kim; Leyah A Schwartz; Jason R Zbieg; Craig E Stivala; Michael J Krische
Journal:  J Am Chem Soc       Date:  2018-12-20       Impact factor: 15.419

4.  Ligand-controlled regiodivergent palladium-catalyzed decarboxylative allylation reaction to access α,α-difluoroketones.

Authors:  Ming-Hsiu Yang; Douglas L Orsi; Ryan A Altman
Journal:  Angew Chem Int Ed Engl       Date:  2015-01-07       Impact factor: 15.336

5.  Enantioselective Intramolecular Allylic Substitution via Synergistic Palladium/Chiral Phosphoric Acid Catalysis: Insight into Stereoinduction through Statistical Modeling.

Authors:  Cheng-Che Tsai; Christopher Sandford; Tao Wu; Buyun Chen; Matthew S Sigman; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-30       Impact factor: 15.336

6.  Diastereocontrol in asymmetric allyl-allyl cross-coupling: stereocontrolled reaction of prochiral allylboronates with prochiral allyl chlorides.

Authors:  Laura A Brozek; Michael J Ardolino; James P Morken
Journal:  J Am Chem Soc       Date:  2011-10-05       Impact factor: 15.419

7.  Tandem Rh-catalysis: decarboxylative β-keto acid and alkyne cross-coupling.

Authors:  Faben A Cruz; Zhiwei Chen; Sarah I Kurtoic; Vy M Dong
Journal:  Chem Commun (Camb)       Date:  2016-04-04       Impact factor: 6.222

8.  Catalytic enantioselective allyl-allyl cross-coupling with a borylated allylboronate.

Authors:  Hai Le; Robert E Kyne; Laura A Brozek; James P Morken
Journal:  Org Lett       Date:  2013-03-19       Impact factor: 6.005

9.  Catalytic stereospecific allyl-allyl cross-coupling of internal allyl electrophiles with AllylB(pin).

Authors:  Hai Le; Amanda Batten; James P Morken
Journal:  Org Lett       Date:  2014-04-04       Impact factor: 6.005

10.  Palladium/N-heterocyclic carbene catalysed regio and diastereoselective reaction of ketones with allyl reagents via inner-sphere mechanism.

Authors:  Da-Chang Bai; Fei-Le Yu; Wan-Ying Wang; Di Chen; Hao Li; Qing-Rong Liu; Chang-Hua Ding; Bo Chen; Xue-Long Hou
Journal:  Nat Commun       Date:  2016-06-10       Impact factor: 14.919
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