Literature DB >> 14967057

The direct catalytic asymmetric mannich reaction.

Armando Córdova1.   

Abstract

The direct catalytic asymmetric addition of unmodified carbonyl compounds to preformed or in situ-generated imines has emerged as a promising new route to optically enriched alpha- and beta-amino acid derivatives, beta-lactams, and 1,2- and gamma-amino alcohols. The direct catalytic asymmetric Mannich reactions are mediated by small organometallic and organic amine catalysts that can achieve levels of selectivity similar to those possible with natural enzymes. The different small-molecule catalysts described here are complementary in their applications. They also complement each other in syn or anti selectivity of the direct asymmetric Mannich reaction. In this Account, we highlight the recent developments in and contributions to this research.

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Year:  2004        PMID: 14967057     DOI: 10.1021/ar030231l

Source DB:  PubMed          Journal:  Acc Chem Res        ISSN: 0001-4842            Impact factor:   22.384


  29 in total

1.  Diastereoselective synthesis of fused [1,3]oxazines from ethyl pyruvate, activated acetylenes and N-heterocycles.

Authors:  Issa Yavari; Anvar Mirzaei; Zinatosadat Hossaini; Sanaz Souri
Journal:  Mol Divers       Date:  2009-07-04       Impact factor: 2.943

2.  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

3.  Enantioselective total synthesis of tricyclic myrmicarin alkaloids.

Authors:  Mohammad Movassaghi; Alison E Ondrus
Journal:  Org Lett       Date:  2005-09-29       Impact factor: 6.005

4.  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

5.  B(C6F5)3-Catalyzed C-H Alkylation of N-Alkylamines Using Silicon Enolates without External Oxidant.

Authors:  Jessica Z Chan; Yejin Chang; Masayuki Wasa
Journal:  Org Lett       Date:  2019-01-29       Impact factor: 6.005

6.  The Mannich reaction of malonates with simple imines catalyzed by bifunctional cinchona alkaloids: enantioselective synthesis of beta-amino acids.

Authors:  Jun Song; Yi Wang; Li Deng
Journal:  J Am Chem Soc       Date:  2006-05-10       Impact factor: 15.419

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

Authors:  Barry M Trost; Tanguy Saget; Chao-I Joey Hung
Journal:  J Am Chem Soc       Date:  2016-03-09       Impact factor: 15.419

8.  Ag-catalyzed diastereo- and enantioselective vinylogous Mannich reactions of alpha-ketoimine esters. Development of a method and investigation of its mechanism.

Authors:  Laura C Wieland; Erika M Vieira; Marc L Snapper; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2009-01-21       Impact factor: 15.419

9.  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

10.  Enantioselective synthesis of SNAP-7941: chiral dihydropyrimidone inhibitor of MCH1-R.

Authors:  Jennifer M Goss; Scott E Schaus
Journal:  J Org Chem       Date:  2008-09-04       Impact factor: 4.354

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