Literature DB >> 27681860

Asymmetric Synthesis of Dipropionate Derivatives through Catalytic Hydrogenation of Enantioenriched E-Ketene Heterodimers.

Shi Chen1, Mukulesh Mondal1, Ahmad A Ibrahim1, Kraig A Wheeler2, Nessan J Kerrigan1.   

Abstract

A highly diastereoselective approach to dipropionate derivatives through Pd/C-catalyzed hydrogenation of enantioenriched E-ketene heterodimers is described. Catalytic hydrogenation of the E-isomer of ketene heterodimer β-lactones (12 examples) provides access to syn,anti-β-lactones (dipropionate derivatives) bearing up to three stereogenic centers (dr up to 49:1), and with excellent transfer of chirality (ee up to >99%).

Entities:  

Keywords:  asymmetric synthesis; catalytic hydrogenation; diastereoselectivity; ketene heterodimer; β-lactone

Year:  2016        PMID： 27681860      PMCID： PMC5035679          DOI： 10.1055/s-0035-1561958

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN： 0039-7881            Impact factor:   3.157


  25 in total

1.  Catalytic, asymmetric synthesis of siphonarienal.

Authors:  M A Calter; W Liao; J A Struss
Journal:  J Org Chem       Date:  2001-11-02       Impact factor: 4.354

2.  Organic-catalyst-mediated cyclopropanation reaction.

Authors:  Charles D Papageorgiou; Steven V Ley; Matthew J Gaunt
Journal:  Angew Chem Int Ed Engl       Date:  2003-02-17       Impact factor: 15.336

3.  Iterative strategies for the synthesis of deoxypropionates.

Authors:  Bjorn ter Horst; Ben L Feringa; Adriaan J Minnaard
Journal:  Chem Commun (Camb)       Date:  2010-03-09       Impact factor: 6.222

4.  Catalytic asymmetric assembly of stereodefined propionate units: an enantioselective total synthesis of (-)-pironetin.

Authors:  Xiaoqiang Shen; Andrew S Wasmuth; Junping Zhao; Cheng Zhu; Scott G Nelson
Journal:  J Am Chem Soc       Date:  2006-06-14       Impact factor: 15.419

5.  Josiphos-catalyzed asymmetric homodimerization of ketoketenes.

Authors:  Ahmad A Ibrahim; Pei-Hsun Wei; Gero D Harzmann; Nessan J Kerrigan
Journal:  J Org Chem       Date:  2010-10-29       Impact factor: 4.354

6.  Asymmetric Synthesis of Deoxypropionate Derivatives via Catalytic Hydrogenolysis of Enantioenriched Z-Ketene Heterodimers.

Authors:  Shi Chen; Ahmad A Ibrahim; Mukulesh Mondal; Anthony J Magee; Adam J Cruz; Kraig A Wheeler; Nessan J Kerrigan
Journal:  Org Lett       Date:  2015-06-23       Impact factor: 6.005

7.  Total synthesis of the immunosupressant (-)-pironetin (PA48153C).

Authors:  G E Keck; C E Knutson; S A Wiles
Journal:  Org Lett       Date:  2001-03-08       Impact factor: 6.005

Review 8.  Modern aldol methods for the total synthesis of polyketides.

Authors:  Bernd Schetter; Rainer Mahrwald
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-20       Impact factor: 15.336

9.  Practical, catalytic, asymmetric synthesis of beta-lactones via a sequential ketene dimerization/hydrogenation process: inhibitors of the thioesterase domain of fatty acid synthase.

Authors:  Vikram C Purohit; Robyn D Richardson; Jeffrey W Smith; Daniel Romo
Journal:  J Org Chem       Date:  2006-06-09       Impact factor: 4.354

10.  Enantioselective addition of amines to ketenes catalyzed by a planar-chiral derivative of PPY: possible intervention of chiral Brønsted-acid catalysis.

Authors:  Brian L Hodous; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2002-08-28       Impact factor: 15.419
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