Literature DB >> 14656087

The direct organocatalytic asymmetric mannich reaction: unmodified aldehydes as nucleophiles.

Wolfgang Notz1, Fujie Tanaka, Shin-Ichi Watanabe, Naidu S Chowdari, James M Turner, Rajeswari Thayumanavan, Carlos F Barbas.   

Abstract

The unprecedented application of unmodified aldehydes as nucleophilic donors in direct catalytic asymmetric Mannich-type reactions is disclosed in a full account. Our efforts in broadening the applicability of chiral pyrrolidine-based catalysts in direct asymmetric Mannich-type reactions led to the highly diastereo- and enantioselective and concise synthesis of functionalized alpha- and beta-amino acids, beta-lactams, and amino alcohols.

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Year:  2003        PMID： 14656087     DOI： 10.1021/jo0347359

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  13 in total

1.  A Diels-Alder Reaction Conducted Within the Parameters of Aqueous Organocatalysis: Still Just Smoke and Mirrors.

Authors:  G Neil Stowe; Kim D Janda
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

2.  Solid-Phase Synthesis of β-Amino Ketones Via DNA-Compatible Organocatalytic Mannich Reactions.

Authors:  Nam Tran-Hoang; Thomas Kodadek
Journal:  ACS Comb Sci       Date:  2018-01-24       Impact factor: 3.784

3.  Direct asymmetric anti-Mannich-type reactions catalyzed by a designed amino acid.

Authors:  Susumu Mitsumori; Haile Zhang; Paul Ha-Yeon Cheong; K N Houk; Fujie Tanaka; Carlos F Barbas
Journal:  J Am Chem Soc       Date:  2006-02-01       Impact factor: 15.419

4.  L-Proline functionalized magnetic nanoparticles: A novel magnetically reusable nanocatalyst for one-pot synthesis of 2,4,6-triarylpyridines.

Authors:  Ali Maleki; Razieh Firouzi-Haji
Journal:  Sci Rep       Date:  2018-11-23       Impact factor: 4.379

5.  L-Proline Functionalized Polymers Prepared by RAFT Polymerization and Their Assemblies as Supported Organocatalysts.

Authors:  Annhelen Lu; Thomas P Smart; Thomas H Epps; Deborah A Longbottom; Rachel K O'Reilly
Journal:  Macromolecules       Date:  2011-09-27       Impact factor: 5.985

6.  Three-component Ag-catalyzed enantioselective vinylogous mannich and Aza-Diels-Alder reactions with alkyl-substituted aldehydes.

Authors:  Hiroki Mandai; Kyoko Mandai; Marc L Snapper; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2008-12-31       Impact factor: 15.419

7.  Towards vast libraries of scaffold-diverse, conformationally constrained oligomers.

Authors:  Thomas Kodadek; Patrick J McEnaney
Journal:  Chem Commun (Camb)       Date:  2016-03-21       Impact factor: 6.222

8.  Pipecolic acid-catalyzed direct asymmetric mannich reactions.

Authors:  Paul Ha-Yeon Cheong; Haile Zhang; Rajee Thayumanavan; Fujie Tanaka; K N Houk; Carlos F Barbas
Journal:  Org Lett       Date:  2006-03-02       Impact factor: 6.005

9.  Second-generation DBFOX ligands for the synthesis of beta-substituted alpha-amino acids via enantioselective radical conjugate additions.

Authors:  Biplab Banerjee; Steven G Capps; Junghoon Kang; Joshua W Robinson; Steven L Castle
Journal:  J Org Chem       Date:  2008-10-24       Impact factor: 4.354

10.  Skeletally diverse small molecules using a build/couple/pair strategy.

Authors:  Takuya Uchida; Manuela Rodriquez; Stuart L Schreiber
Journal:  Org Lett       Date:  2009-04-02       Impact factor: 6.005
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