Literature DB >> 16774225

Catalytic asymmetric addition of dialkylzinc reagents to alpha-aldiminoesters.

Sandeep Basra1, Michael W Fennie, Marisa C Kozlowski.   

Abstract

[reaction: see text] The first catalytic, enantioselective addition of organozinc reagents to alpha-aldiminoesters is described. The use of a Lewis acid/Lewis base containing bifunctional catalyst preorganizes both reactive substrates to promote enantioselective addition over the racemic background reaction and alternative addition modes. Alcohol additives were found to enhance the enantioselection. The addition product was also found to cyclize with remaining substrate to provide imidazolidines.

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Year:  2006        PMID: 16774225      PMCID: PMC3289996          DOI: 10.1021/ol0602093

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


  21 in total

1.  Two syntheses of the 16- and 17-membered DEF ring systems of chloropeptin and complestatin.

Authors:  A M Elder; D H Rich
Journal:  Org Lett       Date:  1999-11-04       Impact factor: 6.005

2.  The first catalytic asymmetric addition of dialkylzincs to alpha-ketoesters.

Authors:  Erin F DiMauro; Marisa C Kozlowski
Journal:  Org Lett       Date:  2002-10-31       Impact factor: 6.005

3.  Development of bifunctional salen catalysts: rapid, chemoselective alkylations of alpha-ketoesters.

Authors:  Erin F DiMauro; Marisa C Kozlowski
Journal:  J Am Chem Soc       Date:  2002-10-30       Impact factor: 15.419

Review 4.  The building block approach to unusual alpha-amino acid derivatives and peptides.

Authors:  Sambasivarao Kotha
Journal:  Acc Chem Res       Date:  2003-05       Impact factor: 22.384

5.  Catalytic enantioselective addition of dialkylzinc to N-diphenylphosphinoylimines. A practical synthesis of alpha-chiral amines.

Authors:  Alessandro A Boezio; André B Charette
Journal:  J Am Chem Soc       Date:  2003-02-19       Impact factor: 15.419

6.  Enantioselective direct-addition of terminal alkynes to imines catalyzed by copper(I)pybox complex in water and in toluene.

Authors:  Chunmei Wei; Chao-Jun Li
Journal:  J Am Chem Soc       Date:  2002-05-22       Impact factor: 15.419

7.  Asymmetric synthesis of quaternary alpha- and beta-amino acids and beta-lactams via proline-catalyzed mannich reactions with branched aldehyde donors.

Authors:  Naidu S Chowdari; Jeff T Suri; Carlos F Barbas
Journal:  Org Lett       Date:  2004-07-22       Impact factor: 6.005

8.  Dimethylzinc-mediated addition of alkenylzirconocenes to alpha-keto and alpha-imino esters.

Authors:  Peter Wipf; Corey R J Stephenson
Journal:  Org Lett       Date:  2003-07-10       Impact factor: 6.005

9.  Optically active aromatic and heteroaromatic alpha-amino acids by a one-pot catalytic enantioselective addition of aromatic and heteroaromatic C-H bonds to alpha-imino esters.

Authors:  Steen Saaby; Pau Bayón; Pompiliu S Aburel; Karl Anker Jørgensen
Journal:  J Org Chem       Date:  2002-06-14       Impact factor: 4.354

Review 10.  The direct catalytic asymmetric mannich reaction.

Authors:  Armando Córdova
Journal:  Acc Chem Res       Date:  2004-02       Impact factor: 22.384

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  5 in total

1.  Formation of C-C Bonds via Iridium-Catalyzed Hydrogenation and Transfer Hydrogenation.

Authors:  John F Bower; Michael J Krische
Journal:  Top Organomet Chem       Date:  2011-01-01       Impact factor: 1.311

2.  Bifunctional asymmetric catalysis: cooperative Lewis acid/base systems.

Authors:  Daniel H Paull; Ciby J Abraham; Michael T Scerba; Ethan Alden-Danforth; Thomas Lectka
Journal:  Acc Chem Res       Date:  2008-04-11       Impact factor: 22.384

3.  Highly Atom Economic Synthesis of d-2-Aminobutyric Acid through an In Vitro Tri-enzymatic Catalytic System.

Authors:  Xi Chen; Yunfeng Cui; Xinkuan Cheng; Jinhui Feng; Qiaqing Wu; Dunming Zhu
Journal:  ChemistryOpen       Date:  2017-07-17       Impact factor: 2.911

4.  Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction.

Authors:  Yiwen Xiong; Haibo Mei; Lingmin Wu; Jianlin Han; Yi Pan; Guigen Li
Journal:  Beilstein J Org Chem       Date:  2014-03-13       Impact factor: 2.883

5.  Asymmetric synthesis of α-allyl-α-aryl α-amino acids by tandem alkylation/π-allylation of α-iminoesters.

Authors:  John M Curto; Joshua S Dickstein; Simon Berritt; Marisa C Kozlowski
Journal:  Org Lett       Date:  2014-03-25       Impact factor: 6.005

  5 in total

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