Literature DB >> 26103052

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

Shi Chen1, Ahmad A Ibrahim1, Mukulesh Mondal1, Anthony J Magee1, Adam J Cruz1, Kraig A Wheeler2, Nessan J Kerrigan1.   

Abstract

A diastereoselective approach to deoxypropionate derivatives through Pd/C-catalyzed hydrogenolysis of enantioenriched ketene heterodimers is described. Catalytic hydrogenolysis of the Z-isomer of ketene heterodimers facilitates access to anti-deoxypropionate derivatives (10 examples with dr 7:1 to >20:1). Transfer of chirality from the Z-ketene heterodimer to an acid product was good to excellent in most cases (78-99% ee for 12 examples).

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Year:  2015        PMID： 26103052      PMCID： PMC4548883          DOI： 10.1021/acs.orglett.5b01391

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


  30 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.  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

3.  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

4.  Chirality and fragrance chemistry: stereoisomers of the commercial chiral odorants Muguesia and Pamplefleur.

Authors:  Agnese Abate; Elisabetta Brenna; Claudio Fuganti; Francesco G Gatti; Tommaso Giovenzana; Luciana Malpezzi; Stefano Serra
Journal:  J Org Chem       Date:  2005-02-18       Impact factor: 4.354

5.  First total synthesis of a natural product containing a chiral, beta-diketone: synthesis and stereochemical reassignment of siphonarienedione and siphonarienolone.

Authors:  Michael A Calter; Wensheng Liao
Journal:  J Am Chem Soc       Date:  2002-11-06       Impact factor: 15.419

6.  Synthesis of hydroxyphthioceranic acid using a traceless lithiation-borylation-protodeboronation strategy.

Authors:  Ramesh Rasappan; Varinder K Aggarwal
Journal:  Nat Chem       Date:  2014-07-27       Impact factor: 24.427

7.  Synthesis of the C(26)-C(32) Oxazole Fragment of Calyculin C: A Test Case for Oxazole Syntheses.

Authors:  Petri M. Pihko; Ari M. P. Koskinen
Journal:  J Org Chem       Date:  1998-01-09       Impact factor: 4.354

8.  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

9.  Application of conformation design in acyclic stereoselection: total synthesis of borrelidin as the crystalline benzene solvate.

Authors:  Stephen Hanessian; Yang Yang; Simon Giroux; Vincent Mascitti; Jianguo Ma; Franck Raeppel
Journal:  J Am Chem Soc       Date:  2003-11-12       Impact factor: 15.419

10.  Catalytic, asymmetric preparation of ketene dimers from acid chlorides.

Authors:  Michael A Calter; Robert K Orr; Wei Song
Journal:  Org Lett       Date:  2003-11-27       Impact factor: 6.005
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  3 in total

1.  Catalytic Asymmetric Synthesis of Ketene Heterodimer β-Lactones: Scope and Limitations.

Authors:  Shi Chen; Ahmad A Ibrahim; Nicholas J Peraino; Divya Nalla; Mukulesh Mondal; Maxwell Van Raaphorst; Nessan J Kerrigan
Journal:  J Org Chem       Date:  2016-08-12       Impact factor: 4.354

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

Authors:  Shi Chen; Mukulesh Mondal; Ahmad A Ibrahim; Kraig A Wheeler; Nessan J Kerrigan
Journal:  Synthesis (Stuttg)       Date:  2016-04-12       Impact factor: 3.157

3.  Molecular Understanding of the Catalytic Consequence of Ketene Intermediates under Confinement.

Authors:  Wei Chen; Guangchao Li; Xianfeng Yi; Sarah J Day; Karolina A Tarach; Zhiqiang Liu; Shang-Bin Liu; Shik Chi Edman Tsang; Kinga Góra-Marek; Anmin Zheng
Journal:  J Am Chem Soc       Date:  2021-09-03       Impact factor: 15.419
  3 in total

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