Literature DB >> 15704962

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

Agnese Abate1, Elisabetta Brenna, Claudio Fuganti, Francesco G Gatti, Tommaso Giovenzana, Luciana Malpezzi, Stefano Serra.   

Abstract

[structure: see text] The work describes the enzyme-mediated preparation and the odor evaluation of the single stereoisomers of the commercial odorants Muguesia and Pamplefleur. The synthetic approach to Muguesia stereoisomers helped to clear the assignment of the relative configuration of intermediate diols 5. The odor response of Pamplefleur isomers was found to be rather unusual. No stereoisomer prevailed, but each one played a definite role in establishing the odor sensation of the final blend.

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Year:  2005        PMID: 15704962     DOI: 10.1021/jo048445j

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  6 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 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

3.  A permutation approach to the assignment of the configuration to diastereomeric tetrads by comparison of experimental and ab initio calculated differences in NMR data.

Authors:  Przemysław J Boratyński
Journal:  Beilstein J Org Chem       Date:  2017-11-22       Impact factor: 2.883

4.  Highly Enantioselective Iridium-Catalyzed Hydrogenation of Conjugated Trisubstituted Enones.

Authors:  Bram B C Peters; Jira Jongcharoenkamol; Suppachai Krajangsri; Pher G Andersson
Journal:  Org Lett       Date:  2020-12-22       Impact factor: 6.005

5.  Reductive enzymatic dynamic kinetic resolution affording 115 g/L (S)-2-phenylpropanol.

Authors:  Christian Rapp; Simone Pival-Marko; Erika Tassano; Bernd Nidetzky; Regina Kratzer
Journal:  BMC Biotechnol       Date:  2021-10-11       Impact factor: 2.563

6.  Stereoselective Iridium-N,P-Catalyzed Double Hydrogenation of Conjugated Enones to Saturated Alcohols.

Authors:  Bram B C Peters; Jia Zheng; Suppachai Krajangsri; Pher G Andersson
Journal:  J Am Chem Soc       Date:  2022-05-05       Impact factor: 16.383

  6 in total

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