Literature DB >> 26952276

Direct Catalytic Asymmetric Mannich Reactions for the Construction of Quaternary Carbon Stereocenters.

Barry M Trost1, Tanguy Saget1, Chao-I Joey Hung1.   

Abstract

Herein, we report a Zn-ProPhenol catalyzed Mannich reaction using α-branched ketones as nucleophilic partners for the direct enantio- and diastereoselective construction of quaternary carbon stereocenters. The reaction can be run on a gram-scale with a low catalyst loading without impacting its efficiency. Moreover, the Mannich adducts can be further elaborated with complete diastereocontrol to access molecules possessing complex stereotriads.

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Year:  2016        PMID： 26952276      PMCID： PMC4866641          DOI： 10.1021/jacs.6b01187

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


  30 in total

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2.  The atom economy--a search for synthetic efficiency.

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Authors:  Manabu Hatano; Takahiro Horibe; Kazuaki Ishihara
Journal:  J Am Chem Soc       Date:  2010-01-13       Impact factor: 15.419

6.  Asymmetric synthesis of quaternary alpha- and beta-amino acids and beta-lactams via proline-catalyzed mannich reactions with branched aldehyde donors.

Authors:  Naidu S Chowdari; Jeff T Suri; Carlos F Barbas
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7.  Enantioselective organocatalytic anti-Mannich-type reaction of N-unprotected 3-substituted 2-oxindoles with aromatic N-Ts-aldimines.

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Authors:  Armando Córdova
Journal:  Acc Chem Res       Date:  2004-02       Impact factor: 22.384

Review 9.  Catalytic asymmetric direct Mannich reaction: a powerful tool for the synthesis of alpha,beta-diamino acids.

Authors:  Ramón Gómez Arrayás; Juan C Carretero
Journal:  Chem Soc Rev       Date:  2009-04-14       Impact factor: 54.564

10.  Organocatalytic highly enantio- and diastereoselective Mannich reaction of beta-ketoesters with N-Boc-aldimines.

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  10 in total

1.  Controlling Regioselectivity in the Enantioselective N-Alkylation of Indole Analogues Catalyzed by Dinuclear Zinc-ProPhenol.

Authors:  Barry M Trost; Elumalai Gnanamani; Chao-I Joey Hung
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-19       Impact factor: 15.336

2.  Efficient Access to Chiral Trisubstituted Aziridines via Catalytic Enantioselective Aza-Darzens Reactions.

Authors:  Barry M Trost; Tanguy Saget; Chao-I Joey Hung
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3.  C-H Functionalization of Amines via Alkene-Derived Nucleophiles through Cooperative Action of Chiral and Achiral Lewis Acid Catalysts: Applications in Enantioselective Synthesis.

Authors:  Ming Shang; Jessica Z Chan; Min Cao; Yejin Chang; Qifan Wang; Brennan Cook; Sebastian Torker; Masayuki Wasa
Journal:  J Am Chem Soc       Date:  2018-08-10       Impact factor: 15.419

4.  Development of bifunctional organocatalysts and application to asymmetric total synthesis of naucleofficine I and II.

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Journal:  Nat Commun       Date:  2019-07-29       Impact factor: 14.919

5.  Asymmetric construction of acyclic quaternary stereocenters via direct enantioselective additions of α-alkynyl ketones to allenamides.

Authors:  Jiawen Wang; Faqian He; Xiaoyu Yang
Journal:  Nat Commun       Date:  2021-11-18       Impact factor: 14.919

Review 6.  Recent advances and prospects in the Zn-catalysed Mannich reaction.

Authors:  Salahudeen Shamna; C M A Afsina; Rose Mary Philip; Gopinathan Anilkumar
Journal:  RSC Adv       Date:  2021-03-01       Impact factor: 3.361

7.  Organocatalytic sulfa-Michael/aldol cascade: constructing functionalized 2,5-dihydrothiophenes bearing a quaternary carbon stereocenter.

Authors:  Xiao-Yu Zhu; Mei-Heng Lv; Ya-Nan Zhao; Li-Yan Lan; Wen-Ze Li; Lin-Jiu Xiao
Journal:  RSC Adv       Date:  2018-10-03       Impact factor: 4.036

8.  Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters.

Authors:  B M Trost; J S Tracy; T Saget
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9.  Mechanism and rate constant of proline-catalysed asymmetric aldol reaction of acetone and p-nitrobenzaldehyde in solution medium: Density-functional theory computation.

Authors:  Usman I Tafida; Adamu Uzairu; Stephen E Abechi
Journal:  J Adv Res       Date:  2018-03-07       Impact factor: 10.479

10.  Multicomponent double Mannich alkylamination involving C(sp2)-H and benzylic C(sp3)-H bonds.

Authors:  Zhencheng Lai; Rongkai Wu; Jiaming Li; Xing Chen; Linwei Zeng; Xi Wang; Jingjing Guo; Zujin Zhao; Hironao Sajiki; Sunliang Cui
Journal:  Nat Commun       Date:  2022-01-21       Impact factor: 14.919
  10 in total

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