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Literature DB >> 23051617

Diastereo- and enantioselective Pd(II)-catalyzed additions of 2-alkylazaarenes to N-Boc imines and nitroalkenes.

Daniel Best¹, Szymon Kujawa, Hon Wai Lam.

Abstract

A chiral Pd(II)-bis(oxazoline) complex was found to be highly effective in promoting the first direct diastereo- and enantioselective addition of alkylazaarenes to N-Boc aldimines and nitroalkenes under mild conditions. Deprotection of Boc-protected products proceeded readily to provide amines in high yields.

Entities: Chemical Gene

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Year: 2012 PMID： 23051617 DOI： 10.1021/ja3083494

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

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Cited

9 in total

1. Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

Authors: Robert Connon; Brendan Roche; Balaji V Rokade; Patrick J Guiry
Journal: Chem Rev Date: 2021-05-21 Impact factor: 60.622

2. Convergent Synthesis of α-Branched Amines by Transition-Metal-Catalyzed C-H Bond Additions to Imines.

Authors: Joshua R Hummel; Jonathan A Ellman
Journal: Isr J Chem Date: 2017-06-29 Impact factor: 3.333

3. Enantioselective direct Mannich-type reactions of 2-benzylpyridine N-oxides catalyzed by chiral bis(guanidino)iminophosphorane organosuperbase.

Authors: Qiupeng Hu; Azusa Kondoh; Masahiro Terada
Journal: Chem Sci Date: 2018-04-20 Impact factor: 9.825

Diastereo- and enantioselective Pd(II)-catalyzed additions of 2-alkylazaarenes to N-Boc imines and nitroalkenes.

1. Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

2. Convergent Synthesis of α-Branched Amines by Transition-Metal-Catalyzed C-H Bond Additions to Imines.

3. Enantioselective direct Mannich-type reactions of 2-benzylpyridine N-oxides catalyzed by chiral bis(guanidino)iminophosphorane organosuperbase.

4. Synergistic catalysis: cis-cyclopropanation of benzoxazoles.

5. A highly site-selective radical sp³ C-H amination of azaheterocycles.

6. Total Synthesis of Shearinines D and G: A Convergent Approach to Indole Diterpenoids.

7. Pyridylic anions are soft nucleophiles in the palladium-catalyzed C(sp³)-H allylation of 4-alkylpyridines.

8. Additive-Free Pd-Catalyzed α-Allylation of Imine-Containing Heterocycles.

9. Acetic Acid Promoted Redox Annulations with Dual C-H Functionalization.