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Literature DB >> 17017786

Catalytic asymmetric reductive amination of aldehydes via dynamic kinetic resolution.

Sebastian Hoffmann¹, Marcello Nicoletti, Benjamin List.

Abstract

A novel organocatalytic asymmetric reductive amination of aldehydes has been developed. Treating racemic alpha-branched aldehydes with p-anisidine and a Hantzsch ester in the presence of our previously developed phosphoric acid catalyst, TRIP, gave beta-branched secondary amines in excellent yields and enantioselectivities via an efficient dynamic kinetic resolution. The process is applicable to several different aromatic aldehydes and amines but gives slightly reduced enantiomeric ratios with aliphatic aldehydes.

Entities: Chemical

Year: 2006 PMID： 17017786 DOI： 10.1021/ja065404r

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

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Cited

14 in total

1. Dynamic Kinetic Resolution of Aldehydes by Hydroacylation.

Authors: Zhiwei Chen; Yusuke Aota; Hillary M H Nguyen; Vy M Dong
Journal: Angew Chem Int Ed Engl Date: 2019-02-27 Impact factor: 15.336

2. Enantioselective synthesis of anti- and syn-homopropargyl alcohols via chiral Brønsted acid catalyzed asymmetric allenylboration reactions.

Authors: Ming Chen; William R Roush
Journal: J Am Chem Soc Date: 2012-06-25 Impact factor: 15.419

3. Chiral Brønsted Acid Catalyzed Kinetic Resolutions.

Authors: Kimberly S Petersen
Journal: Asian J Org Chem Date: 2016-03-07 Impact factor: 3.319

4. Enamine/Carbene Cascade Catalysis in the Diastereo- and Enantioselective Synthesis of Functionalized Cyclopentanones.

Authors: Kerem E Ozboya; Tomislav Rovis
Journal: Chem Sci Date: 2011-09-01 Impact factor: 9.825

5. Catalytic dynamic kinetic resolutions with N-heterocyclic carbenes: asymmetric synthesis of highly substituted β-lactones.

Authors: Daniel T Cohen; Chad C Eichman; Eric M Phillips; Emily R Zarefsky; Karl A Scheidt
Journal: Angew Chem Int Ed Engl Date: 2012-06-14 Impact factor: 15.336

6. Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations.

Authors: Vikram Bhat; Eric R Welin; Xuelei Guo; Brian M Stoltz
Journal: Chem Rev Date: 2017-02-06 Impact factor: 60.622

Catalytic asymmetric reductive amination of aldehydes via dynamic kinetic resolution.

1. Dynamic Kinetic Resolution of Aldehydes by Hydroacylation.

2. Enantioselective synthesis of anti- and syn-homopropargyl alcohols via chiral Brønsted acid catalyzed asymmetric allenylboration reactions.

3. Chiral Brønsted Acid Catalyzed Kinetic Resolutions.

4. Enamine/Carbene Cascade Catalysis in the Diastereo- and Enantioselective Synthesis of Functionalized Cyclopentanones.

5. Catalytic dynamic kinetic resolutions with N-heterocyclic carbenes: asymmetric synthesis of highly substituted β-lactones.

6. Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations.

7. Synthesis of Complex Tertiary Glycolates by Enantioconvergent Arylation of Stereochemically Labile α-Keto Esters.

8. Divergent Stereoselectivity in Phosphothreonine (pThr)-Catalyzed Reductive Aminations of 3-Amidocyclohexanones.

9. A Sequential Umpolung/Enzymatic Dynamic Kinetic Resolution Strategy for the Synthesis of γ-Lactones.

10. Highly enantioselective hydrogenation of enamides catalyzed by chiral phosphoric acids.