Literature DB >> 12405820

Asymmetric catalytic Mannich reactions catalyzed by urea derivatives: enantioselective synthesis of beta-aryl-beta-amino acids.

Anna G Wenzel1, Eric N Jacobsen.   

Abstract

Highly enantioselective addition reactions between silyl ketene acetals and N-Boc aldimines are catalyzed by the thiourea-based catalyst 1c. Extraordinary scope is observed in this methodology with regard to the imine substrate, with aryl and heteroaromatic derivatives generally affording nearly quantitative yields of beta-amino ester product in up to 98% enantioselectivity.

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Year:  2002        PMID: 12405820     DOI: 10.1021/ja028353g

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


  25 in total

1.  Enantioselective Synthesis of β-Amino Acid Derivatives Enabled by Ligand-Controlled Reversal of Hydrocupration Regiochemistry.

Authors:  Sheng Guo; Jiaqi Zhu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2020-09-11       Impact factor: 15.336

2.  Thiourea-catalyzed enantioselective cyanosilylation of ketones.

Authors:  Douglas E Fuerst; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2005-06-29       Impact factor: 15.419

3.  Formal [4 + 2] cycloaddition of imines with alkoxyisocoumarins.

Authors:  Claire L Jarvis; Neyra M Jemal; Spencer Knapp; Daniel Seidel
Journal:  Org Biomol Chem       Date:  2018-06-13       Impact factor: 3.876

4.  Chiral β-Iodoamines by Urea-Catalyzed Iodocyclization of Trichloroacetimidates.

Authors:  Cheyenne S Brindle; Charles S Yeung; Eric N Jacobsen
Journal:  Chem Sci J       Date:  2013-05-01

5.  Room-temperature enantioselective C-H iodination via kinetic resolution.

Authors:  Ling Chu; Kai-Jiong Xiao; Jin-Quan Yu
Journal:  Science       Date:  2014-10-24       Impact factor: 47.728

6.  Practical and highly enantioselective synthesis of beta-alkynyl-beta-amino esters through Ag-catalyzed asymmetric mannich reactions of silylketene acetals and alkynyl imines.

Authors:  Nathan S Josephsohn; Emma L Carswell; Marc L Snapper; Amir H Hoveyda
Journal:  Org Lett       Date:  2005-06-23       Impact factor: 6.005

7.  Bronsted acid catalysis of achiral enamine for regio- and enantioselective nitroso aldol synthesis.

Authors:  Norie Momiyama; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2005-02-02       Impact factor: 15.419

8.  Mannich-type Reactions of Cyclic Nitrones: Effective Methods for the Enantioselective Synthesis of Piperidine-containing Alkaloids.

Authors:  Vladislav G Lisnyak; Tessa Lynch-Colameta; Scott A Snyder
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-19       Impact factor: 15.336

9.  Enantioselective, thiourea-catalyzed intermolecular addition of indoles to cyclic N-acyl iminium ions.

Authors:  Emily A Peterson; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  Diastereoselective and enantioselective synthesis of tertiary alpha-hydroxy phosphonates through hydrogen-bond catalysis.

Authors:  Vijaya Bhasker Gondi; Koji Hagihara; Viresh H Rawal
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

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