Literature DB >> 12203627

Catalytic Asymmetric Direct Mannich Reactions of Carbonyl Compounds with α-Imino Esters.

K Juhl1, N Gathergood, K A Jørgensen.   

Abstract

The development of a direct catalytic asymmetric Mannich reaction is shown and its potential demonstrated by the synthesis of optically active lactones via 4-hydroxyglutamic acid ester derivatives. The catalytic asymmetric Mannich reaction of carbonyl compounds with α-imino esters [Eq. (1); Ts = p-toluenesulfonyl] gives good yields and diastereoselectivities, as well as excellent enantioselectivities.
Copyright © 2001 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany.

Entities:  

Keywords:  Lewis acids; Mannich reactions; amino acids; asymmetric catalysis; imines

Year:  2001        PMID： 12203627     DOI： 10.1002/1521-3773(20010817)40:16<2995::AID-ANIE2995>3.0.CO;2-M

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  8 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.  Synthesis and Reactivity of α-Haloglycine Esters: Hyperconjugation in Action.

Authors:  Shyam S Samanta; Stéphane P Roche
Journal:  European J Org Chem       Date:  2019-08-24

Review 3.  Expanding lysine industry: industrial biomanufacturing of lysine and its derivatives.

Authors:  Jie Cheng; Peng Chen; Andong Song; Dan Wang; Qinhong Wang
Journal:  J Ind Microbiol Biotechnol       Date:  2018-04-13       Impact factor: 3.346

4.  In Situ-Generated Glycinyl Chloroaminals for a One-Pot Synthesis of Non-proteinogenic α-Amino Esters.

Authors:  Shyam S Samanta; Stéphane P Roche
Journal:  J Org Chem       Date:  2017-08-04       Impact factor: 4.354

5.  Catalytic asymmetric addition of dialkylzinc reagents to alpha-aldiminoesters.

Authors:  Sandeep Basra; Michael W Fennie; Marisa C Kozlowski
Journal:  Org Lett       Date:  2006-06-22       Impact factor: 6.005

6.  A direct catalytic asymmetric Mannich-type reaction via a dinuclear zinc catalyst: synthesis of either anti- or syn-alpha-hydroxy-beta-amino ketones.

Authors:  Barry M Trost; Jaray Jaratjaroonphong; Vichai Reutrakul
Journal:  J Am Chem Soc       Date:  2006-03-08       Impact factor: 15.419

7.  Synthesis of Structurally Diverse 3-, 4-, 5-, and 6-Membered Heterocycles from Diisopropyl Iminomalonates and Soft C-Nucleophiles.

Authors:  Padmanabha V Kattamuri; Urmibhusan Bhakta; Surached Siriwongsup; Doo-Hyun Kwon; Lawrence B Alemany; Muhammed Yousufuddin; Daniel H Ess; László Kürti
Journal:  J Org Chem       Date:  2019-05-14       Impact factor: 4.354

8.  Pd-catalyzed asymmetric allylic alkylations via C-H activation of N-allyl imines with glycinates.

Authors:  Barry M Trost; Xiaoxun Li
Journal:  Chem Sci       Date:  2017-08-15       Impact factor: 9.825
  8 in total

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