Literature DB >> 32422045

Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Acyclic α-N-Pyrrolyl/Indolyl Ketones.

Remi Lavernhe1, Eric J Alexy1, Haiming Zhang2, Brian M Stoltz1.   

Abstract

The synthesis of fully substituted α-N-pyrrolyl and indolyl ketones via enantioselective palladium-catalyzed allylic alkylation is described. The acyclic ketones are alkylated in high yields with high enantioselectivities through the use of an electron-deficient phosphinooxazoline ligand, furnishing a highly congested and synthetically challenging stereocenter. The obtained alkylation products contain multiple reactive sites poised for additional functionalizations and diversification.

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Year:  2020        PMID： 32422045      PMCID： PMC7608871          DOI： 10.1021/acs.orglett.0c01303

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  29 in total

1.  Enantioselective intramolecular aza-Michael additions of indoles catalyzed by chiral phosphoric acids.

Authors:  Quan Cai; Chao Zheng; Shu-Li You
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-08       Impact factor: 15.336

2.  Palladium-Catalyzed Asymmetric Nitrogen-Selective Addition Reaction of Indoles to Alkoxyallenes.

Authors:  Seok Hyeon Jang; Hyun Woo Kim; Wook Jeong; Dohyun Moon; Young Ho Rhee
Journal:  Org Lett       Date:  2018-02-05       Impact factor: 6.005

3.  Enantioselective Construction of Acyclic Quaternary Carbon Stereocenters: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Amide Enolates.

Authors:  Pavel Starkov; Jared T Moore; Douglas C Duquette; Brian M Stoltz; Ilan Marek
Journal:  J Am Chem Soc       Date:  2017-07-07       Impact factor: 15.419

4.  Lithium Hexamethyldisilazide-Mediated Enolization of Highly Substituted Aryl Ketones: Structural and Mechanistic Basis of the E/Z Selectivities.

Authors:  Kyle A Mack; Andrew McClory; Haiming Zhang; Francis Gosselin; David B Collum
Journal:  J Am Chem Soc       Date:  2017-08-23       Impact factor: 15.419

5.  Catalytic Asymmetric N-Alkylation of Indoles and Carbazoles through 1,6-Conjugate Addition of Aza-para-quinone Methides.

Authors:  Min Chen; Jianwei Sun
Journal:  Angew Chem Int Ed Engl       Date:  2017-03-23       Impact factor: 15.336

6.  Palladium-catalyzed α,β-dehydrogenation of acyclic ester equivalents promoted by a novel electron deficient phosphinooxazoline ligand.

Authors:  Tyler J Fulton; Brenda Wu; Eric J Alexy; Haiming Zhang; Brian M Stoltz
Journal:  Tetrahedron       Date:  2019-06-01       Impact factor: 2.457

7.  Chemo-, regio-, and enantioselective Pd-catalyzed allylic alkylation of indolocarbazole pro-aglycons.

Authors:  Barry M Trost; Michael J Krische; Volker Berl; Ellen M Grenzer
Journal:  Org Lett       Date:  2002-06-13       Impact factor: 6.005

8.  Asymmetric organocatalytic N-alkylation of indole-2-carbaldehydes with alpha,beta-unsaturated aldehydes: one-pot synthesis of chiral pyrrolo[1,2-a]indole-2-carbaldehydes.

Authors:  Liang Hong; Wangsheng Sun; Chunxia Liu; Lei Wang; Rui Wang
Journal:  Chemistry       Date:  2010-01-11       Impact factor: 5.236

9.  Flinderoles A-C: antimalarial bis-indole alkaloids from Flindersia species.

Authors:  Liza S Fernandez; Malcolm S Buchanan; Anthony R Carroll; Yun Jiang Feng; Ronald J Quinn; Vicky M Avery
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

10.  Enantioconvergent Alkylations of Amines by Alkyl Electrophiles: Copper-Catalyzed Nucleophilic Substitutions of Racemic α-Halolactams by Indoles.

Authors:  Agnieszka Bartoszewicz; Carson D Matier; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2019-09-09       Impact factor: 15.419
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  2 in total

1.  Catalytic Enantioselective Synthesis of α-Difunctionalized Cyclic Sulfones.

Authors:  Eleanor Bowen; Gillian Laidlaw; Bethany C Atkinson; Timur A McArdle-Ismaguilov; Vilius Franckevičius
Journal:  J Org Chem       Date:  2022-07-08       Impact factor: 4.198

2.  Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of Thietane 1,1-Dioxides.

Authors:  Gillian Laidlaw; Vilius Franckevičius
Journal:  Org Lett       Date:  2021-12-16       Impact factor: 6.005
  2 in total

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