Literature DB >> 19886612

Chiral Brønsted acid-catalyzed enantioselective multicomponent Mannich reaction: synthesis of anti-1,3-diamines using enecarbamates as nucleophiles.

Guillaume Dagousset1, Fleur Drouet, Géraldine Masson, Jieping Zhu.   

Abstract

Reaction of aldehydes 2, anilines 3, and enecarbamates 4 in dichloromethane in the presence of EtOH and a catalytic amount of chiral phosphoric acid 5 afforded the Mannich adducts which were in situ reduced to anti-1,2-disubstituted 1,3-diamines 1 in excellent diastereoselectivity and enantioselectivity.

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Year:  2009        PMID： 19886612     DOI： 10.1021/ol9023985

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  6 in total

1.  1,4-Diazaspiro[2.2]pentanes as a flexible platform for the synthesis of diamine-bearing stereotriads.

Authors:  Jared W Rigoli; Luke A Boralsky; John C Hershberger; Dagmara Marston; Alan R Meis; Ilia A Guzei; Jennifer M Schomaker
Journal:  J Org Chem       Date:  2012-02-14       Impact factor: 4.354

2.  Synthesis of 1,3-diaminated stereotriads via rearrangement of 1,4-diazaspiro[2.2]pentanes.

Authors:  Cale D Weatherly; Jared W Rigoli; Jennifer M Schomaker
Journal:  Org Lett       Date:  2012-03-20       Impact factor: 6.005

3.  N-triflylthiophosphoramide catalyzed enantioselective Mukaiyama aldol reaction of aldehydes with silyl enol ethers of ketones.

Authors:  Cheol Hong Cheon; Hisashi Yamamoto
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

4.  Selecting Chiral BINOL-Derived Phosphoric Acid Catalysts: General Model To Identify Steric Features Essential for Enantioselectivity.

Authors:  Jolene P Reid; Jonathan M Goodman
Journal:  Chemistry       Date:  2017-09-14       Impact factor: 5.236

Review 5.  Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis.

Authors:  Brenno A D Neto; Rafael O Rocha; Marcelo O Rodrigues
Journal:  Molecules       Date:  2021-12-27       Impact factor: 4.411

6.  Dinuclear PhosphoiminoBINOL-Pd Container for Malononitrile: Catalytic Asymmetric Double Mannich Reaction for Chiral 1,3-Diamine Synthesis.

Authors:  Takayoshi Arai; Katsuya Sato; Ayu Nakamura; Hiroki Makino; Hyuma Masu
Journal:  Sci Rep       Date:  2018-01-16       Impact factor: 4.379
  6 in total

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