Literature DB >> 26849354

Enantioselective Decarboxylative Arylation of α-Amino Acids via the Merger of Photoredox and Nickel Catalysis.

Zhiwei Zuo1, Huan Cong2, Wei Li1, Junwon Choi2, Gregory C Fu2, David W C MacMillan1.   

Abstract

An asymmetric decarboxylative Csp(3)-Csp(2) cross-coupling has been achieved via the synergistic merger of photoredox and nickel catalysis. This mild, operationally simple protocol transforms a wide variety of naturally abundant α-amino acids and readily available aryl halides into valuable chiral benzylic amines in high enantiomeric excess, thereby producing motifs found in pharmacologically active agents.

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Year:  2016        PMID： 26849354      PMCID： PMC4862596          DOI： 10.1021/jacs.5b13211

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


  34 in total

Review 1.  Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors:  Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal:  Chem Rev       Date:  2013-03-19       Impact factor: 60.622

Review 2.  Repaglinide: a review of its use in type 2 diabetes mellitus.

Authors:  Lesley J Scott
Journal:  Drugs       Date:  2012-01-22       Impact factor: 9.546

3.  Enantioselective reduction of imines catalyzed by a rhenium(V)-oxo complex.

Authors:  Kristine A Nolin; Richard W Ahn; F Dean Toste
Journal:  J Am Chem Soc       Date:  2005-09-14       Impact factor: 15.419

4.  Dual catalysis. Merging photoredox with nickel catalysis: coupling of α-carboxyl sp³-carbons with aryl halides.

Authors:  Zhiwei Zuo; Derek T Ahneman; Lingling Chu; Jack A Terrett; Abigail G Doyle; David W C MacMillan
Journal:  Science       Date:  2014-06-05       Impact factor: 47.728

5.  Catalytic asymmetric α-acylation of tertiary amines mediated by a dual catalysis mode: N-heterocyclic carbene and photoredox catalysis.

Authors:  Daniel A DiRocco; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2012-05-02       Impact factor: 15.419

6.  Highly diastereoselective arylations of substituted piperidines.

Authors:  Stephanie Seel; Tobias Thaler; Keishi Takatsu; Cong Zhang; Hendrik Zipse; Bernd F Straub; Peter Mayer; Paul Knochel
Journal:  J Am Chem Soc       Date:  2011-03-09       Impact factor: 15.419

7.  Enantioselective alkenylation via nickel-catalyzed cross-coupling with organozirconium reagents.

Authors:  Sha Lou; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2010-04-14       Impact factor: 15.419

8.  Enantioselective photoredox catalysis enabled by proton-coupled electron transfer: development of an asymmetric aza-pinacol cyclization.

Authors:  Lydia J Rono; Hatice G Yayla; David Y Wang; Michael F Armstrong; Robert R Knowles
Journal:  J Am Chem Soc       Date:  2013-11-13       Impact factor: 15.419

9.  Ligand-controlled asymmetric arylation of aliphatic α-amino anion equivalents.

Authors:  Ye Zhu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2014-03-13       Impact factor: 15.419

10.  Carboxylic acids as a traceless activation group for conjugate additions: a three-step synthesis of (±)-pregabalin.

Authors:  Lingling Chu; Chisa Ohta; Zhiwei Zuo; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2014-07-28       Impact factor: 15.419
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  54 in total

1.  Nickel-Catalyzed Asymmetric Reductive Cross-Coupling To Access 1,1-Diarylalkanes.

Authors:  Kelsey E Poremba; Nathaniel T Kadunce; Naoyuki Suzuki; Alan H Cherney; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2017-04-13       Impact factor: 15.419

2.  Photoredox-catalyzed Direct Reductive Amination of Aldehydes without an External Hydrogen/Hydride Source.

Authors:  Rauful Alam; Gary A Molander
Journal:  Org Lett       Date:  2018-04-13       Impact factor: 6.005

3.  Forging C(sp3)-C(sp3) Bonds with Carbon-Centered Radicals in the Synthesis of Complex Molecules.

Authors:  Spencer P Pitre; Nicholas A Weires; Larry E Overman
Journal:  J Am Chem Soc       Date:  2019-01-04       Impact factor: 15.419

4.  Photoredox-Catalyzed Site-Selective α-C(sp3 )-H Alkylation of Primary Amine Derivatives.

Authors:  Melissa A Ashley; Chiaki Yamauchi; John C K Chu; Shinya Otsuka; Hideki Yorimitsu; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-15       Impact factor: 15.336

5.  2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones.

Authors:  Kangnan Li; Xinxin Shao; Luke Tseng; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2018-01-04       Impact factor: 15.419

6.  Homologation of α-aryl amino acids through quinone-catalyzed decarboxylation/Mukaiyama-Mannich addition.

Authors:  Benjamin J Haugeberg; Johnny H Phan; Xinyun Liu; Thomas J O'Connor; Michael D Clift
Journal:  Chem Commun (Camb)       Date:  2017-03-09       Impact factor: 6.222

7.  Nickel-Catalyzed Enantioselective Reductive Cross-Coupling Reactions.

Authors:  Kelsey E Poremba; Sara E Dibrell; Sarah E Reisman
Journal:  ACS Catal       Date:  2020-06-24       Impact factor: 13.084

8.  Profiling and Application of Photoredox C(sp3)-C(sp2) Cross-Coupling in Medicinal Chemistry.

Authors:  Rui Zhang; Guoqing Li; Michael Wismer; Petr Vachal; Steven L Colletti; Zhi-Cai Shi
Journal:  ACS Med Chem Lett       Date:  2018-05-07       Impact factor: 4.345

9.  A Dual Palladium and Copper Hydride Catalyzed Approach for Alkyl-Aryl Cross-Coupling of Aryl Halides and Olefins.

Authors:  Stig D Friis; Michael T Pirnot; Lauren N Dupuis; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-16       Impact factor: 15.336

10.  Highly Diastereoselective Functionalization of Piperidines by Photoredox-Catalyzed α-Amino C-H Arylation and Epimerization.

Authors:  Morgan M Walker; Brian Koronkiewicz; Shuming Chen; K N Houk; James M Mayer; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2020-04-24       Impact factor: 15.419
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