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Literature DB >> 34145705

Enantioselective Addition of Pyrazoles to Dienes*.

Alexander Y Jiu¹, Hannah S Slocumb¹, Charles S Yeung², Xiao-Hui Yang³, Vy M Dong¹.

Abstract

We report the first enantioselective addition of pyrazoles to 1,3-dienes. Secondary and tertiary allylic pyrazoles can be generated with excellent regioselectivity. Mechanistic studies support a pathway distinct from previous hydroaminations: a Pd0 -catalyzed ligand-to-ligand hydrogen transfer (LLHT). This hydroamination tolerates a range of functional groups and advances the field of diene hydrofunctionalization.

Entities: Chemical

Keywords: 1,3-diene; Pd-catalysis; enantioselectivity; hydroamination; pyrazole

Mesh：

Substances：

Year: 2021 PMID： 34145705 PMCID： PMC8889753 DOI： 10.1002/anie.202105679

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 16.823

29 in total

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Journal: J Am Chem Soc Date: 2001-05-09 Impact factor: 15.419

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Journal: Chem Rev Date: 1996-02-01 Impact factor: 60.622

3. Variable Time Normalization Analysis: General Graphical Elucidation of Reaction Orders from Concentration Profiles.

Authors: Jordi Burés
Journal: Angew Chem Int Ed Engl Date: 2016-11-25 Impact factor: 15.336

Review 4. Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among U.S. FDA approved pharmaceuticals.

Authors: Edon Vitaku; David T Smith; Jon T Njardarson
Journal: J Med Chem Date: 2014-10-07 Impact factor: 7.446

5. Regio- and enantioselective synthesis of N-substituted pyrazoles by rhodium-catalyzed asymmetric addition to allenes.

Authors: Alexander M Haydl; Kun Xu; Bernhard Breit
Journal: Angew Chem Int Ed Engl Date: 2015-04-29 Impact factor: 15.336

6. Orthogonal Regulation of Nucleophilic and Electrophilic Sites in Pd-Catalyzed Regiodivergent Couplings between Indazoles and Isoprene.

Authors: Wen-Shuang Jiang; Ding-Wei Ji; Wei-Song Zhang; Gong Zhang; Xiang-Ting Min; Yan-Cheng Hu; Xu-Liang Jiang; Qing-An Chen
Journal: Angew Chem Int Ed Engl Date: 2021-03-05 Impact factor: 15.336

7. Ni-Catalyzed Enantioselective Intermolecular Hydroamination of Branched 1,3-Dienes Using Primary Aliphatic Amines.

Authors: Gaël Tran; Wen Shao; Clément Mazet
Journal: J Am Chem Soc Date: 2019-09-04 Impact factor: 15.419

8. Palladium-Catalyzed Regio- and Enantioselective Hydrosulfonylation of 1,3-Dienes with Sulfinic Acids: Scope, Mechanism, and Origin of Selectivity.

Authors: Qinglong Zhang; Dongfang Dong; Weiwei Zi
Journal: J Am Chem Soc Date: 2020-09-03 Impact factor: 15.419