Literature DB >> 15957928

Practical and highly enantioselective synthesis of beta-alkynyl-beta-amino esters through Ag-catalyzed asymmetric mannich reactions of silylketene acetals and alkynyl imines.

Nathan S Josephsohn1, Emma L Carswell, Marc L Snapper, Amir H Hoveyda.   

Abstract

[reaction: see text] A readily available iso-leucine-based phosphine ligand is used to promote Ag-catalyzed Mannich reactions between silylketene acetals and various alkynyl imines. Reactions can be effected in the presence of 5 mol % catalyst, without the need for rigorous exclusion of air, and with commercially available solvents (without purification) to afford the desired beta-alkynyl-beta-amino esters in 84-94% ee and 61-91% isolated yield.

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Year:  2005        PMID： 15957928      PMCID： PMC2597397          DOI： 10.1021/ol050910r

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


  31 in total

1.  A bisphosphepine ligand with stereogenic phosphorus centers for the practical synthesis of beta-aryl-beta-amino acids by asymmetric hydrogenation.

Authors:  Wenjun Tang; Weimin Wang; Yongxiang Chi; Xumu Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2003-08-04       Impact factor: 15.336

Review 2.  Recent developments in the catalytic asymmetric synthesis of alpha- and beta-amino acids.

Authors:  Jun-An Ma
Journal:  Angew Chem Int Ed Engl       Date:  2003-09-22       Impact factor: 15.336

3.  Highly enantioselective one-pot, three-component imino-Reformatsky reaction.

Authors:  Pier Giorgio Cozzi; Eleonora Rivalta
Journal:  Angew Chem Int Ed Engl       Date:  2005-06-06       Impact factor: 15.336

4.  Efficient and practical Ag-catalyzed cycloadditions between arylimines and the Danishefsky diene.

Authors:  Nathan S Josephsohn; Marc L Snapper; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2003-04-09       Impact factor: 15.419

5.  Highly effective chiral ortho-substituted BINAPO ligands (o-BINAPO): applications in Ru-catalyzed asymmetric hydrogenations of beta-aryl-substituted beta-(acylamino)acrylates and beta-keto esters.

Authors:  Yong-Gui Zhou; Wenjun Tang; Wen-Bo Wang; Wenge Li; Xumu Zhang
Journal:  J Am Chem Soc       Date:  2002-05-08       Impact factor: 15.419

6.  Catalytic, asymmetric Mannich-type reactions of N-acylimino esters: reactivity, diastereo- and enantioselectivity, and application to synthesis of N-acylated amino acid derivatives.

Authors:  Shū Kobayashi; Ryosuke Matsubara; Yoshitaka Nakamura; Hidetoshi Kitagawa; Masaharu Sugiura
Journal:  J Am Chem Soc       Date:  2003-03-05       Impact factor: 15.419

7.  Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation.

Authors:  Daisuke Uraguchi; Masahiro Terada
Journal:  J Am Chem Soc       Date:  2004-05-05       Impact factor: 15.419

8.  Enantioselective synthesis of alpha,beta-disubstituted-beta-amino acids.

Authors:  Mukund P Sibi; Narayanasamy Prabagaran; Sandeep G Ghorpade; Craig P Jasperse
Journal:  J Am Chem Soc       Date:  2003-10-01       Impact factor: 15.419

9.  Three-component enantioselective synthesis of propargylamines through Zr-catalyzed additions of alkyl zinc reagents to alkynylimines.

Authors:  Laura C Akullian; Marc L Snapper; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2003-09-15       Impact factor: 15.336

10.  Catalytic asymmetric synthesis of a nitrogen analogue of dialkyl tartrate by direct mannich reaction under phase-transfer conditions.

Authors:  Takashi Ooi; Minoru Kameda; Jun-Ichi Fujii; Keiji Maruoka
Journal:  Org Lett       Date:  2004-07-08       Impact factor: 6.005
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  4 in total

1.  N-Substituted tertiary and O-substituted quaternary carbon stereogenic centers by site-, diastereo- and enantioselective vinylogous Mannich reactions.

Authors:  Daniel L Silverio; Peng Fu; Emma L Carswell; Marc L Snapper; Amir H Hoveyda
Journal:  Tetrahedron Lett       Date:  2015-04-09       Impact factor: 2.415

2.  C-F Bond Formation for the Synthesis of Aryl Fluorides.

Authors:  Takeru Furuya; Johannes E M N Klein; Tobias Ritter
Journal:  Synthesis (Stuttg)       Date:  2010-06-01       Impact factor: 3.157

3.  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

4.  Asymmetric synthesis of syn-propargylamines and unsaturated β-amino acids under Brønsted base catalysis.

Authors:  Yingcheng Wang; Mingjie Mo; Kongxi Zhu; Chao Zheng; Hongbin Zhang; Wei Wang; Zhihui Shao
Journal:  Nat Commun       Date:  2015-10-01       Impact factor: 14.919
  4 in total

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