View in EDS

Asymmetric Synthesis and Absolute Configuration Determination of an Enantioenriched Alcohol: A Discovery-Based Undergraduate Laboratory Experiment

Saved in:
Bibliographic Details
Title: Asymmetric Synthesis and Absolute Configuration Determination of an Enantioenriched Alcohol: A Discovery-Based Undergraduate Laboratory Experiment
Language: English
Authors: King, Ryan P. (ORCID 0000-0002-0798-313X), Wagner, Alexander J., Burtea, Alexander, King, Susan M. (ORCID 0000-0002-4070-1966)
Source: Journal of Chemical Education. Mar 2020 97(3):793-800.
Availability: Division of Chemical Education, Inc. and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Peer Reviewed: Y
Page Count: 8
Publication Date: 2020
Document Type: Journal Articles
Reports - Descriptive
Education Level: Higher Education
Postsecondary Education
Descriptors: Science Instruction, College Science, Undergraduate Study, Organic Chemistry, Scientific Concepts, Science Experiments, Science Laboratories, Laboratory Experiments
DOI: 10.1021/acs.jchemed.9b00872
ISSN: 0021-9584
Abstract: An undergraduate organic chemistry experiment has been developed that features asymmetric synthesis of an enantioenriched secondary alcohol, followed by determination of its absolute configuration using the competing enantioselective conversion (CEC) method. Students are given a ketone and an unknown enantiomer of CBS (Corey-Bakshi-Shibata) catalyst. This reaction forms an enantioenriched secondary alcohol of unknown absolute configuration. Students then determine the absolute configuration via the CEC method. The CEC method is a modern application of the Horeau method that runs parallel reactions using both enantiomers of a chiral acyl-transfer catalyst, homobenzotetramisole (HBTM). Reactions are quenched concurrently, and reaction rates are compared using thin-layer chromatography (TLC) and/or [superscript 1]H nuclear magnetic resonance (NMR) spectroscopy to determine the fast and the slow reactions. By comparing the faster reaction to a previously determined mnemonic, the absolute configuration of the alcohol can be determined. From this information, students can then determine which enantiomer of CBS catalyst they used to form the enantioenriched alcohol. Both parts of this experiment were successfully completed in one 5 h lab section. This experiment provides an opportunity for discussion of important chemistry concepts including asymmetric synthesis, asymmetric catalysis, kinetic resolution, mechanism, transition state theory, and inert-atmosphere techniques.
Abstractor: As Provided
Entry Date: 2020
Accession Number: EJ1248701
Database: ERIC
FullText Text:
  Availability: 0
Header DbId: eric
DbLabel: ERIC
An: EJ1248701
AccessLevel: 3
PubType: Academic Journal
PubTypeId: academicJournal
PreciseRelevancyScore: 0
IllustrationInfo
Items – Name: Title
  Label: Title
  Group: Ti
  Data: Asymmetric Synthesis and Absolute Configuration Determination of an Enantioenriched Alcohol: A Discovery-Based Undergraduate Laboratory Experiment
– Name: Language
  Label: Language
  Group: Lang
  Data: English
– Name: Author
  Label: Authors
  Group: Au
  Data: <searchLink fieldCode="AR" term="%22King%2C+Ryan+P%2E%22">King, Ryan P.</searchLink> (ORCID <externalLink term="http://orcid.org/0000-0002-0798-313X">0000-0002-0798-313X</externalLink>)<br /><searchLink fieldCode="AR" term="%22Wagner%2C+Alexander+J%2E%22">Wagner, Alexander J.</searchLink><br /><searchLink fieldCode="AR" term="%22Burtea%2C+Alexander%22">Burtea, Alexander</searchLink><br /><searchLink fieldCode="AR" term="%22King%2C+Susan+M%2E%22">King, Susan M.</searchLink> (ORCID <externalLink term="http://orcid.org/0000-0002-4070-1966">0000-0002-4070-1966</externalLink>)
– Name: TitleSource
  Label: Source
  Group: Src
  Data: <searchLink fieldCode="SO" term="%22Journal+of+Chemical+Education%22"><i>Journal of Chemical Education</i></searchLink>. Mar 2020 97(3):793-800.
– Name: Avail
  Label: Availability
  Group: Avail
  Data: Division of Chemical Education, Inc. and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
– Name: PeerReviewed
  Label: Peer Reviewed
  Group: SrcInfo
  Data: Y
– Name: Pages
  Label: Page Count
  Group: Src
  Data: 8
– Name: DatePubCY
  Label: Publication Date
  Group: Date
  Data: 2020
– Name: TypeDocument
  Label: Document Type
  Group: TypDoc
  Data: Journal Articles<br />Reports - Descriptive
– Name: Audience
  Label: Education Level
  Group: Audnce
  Data: <searchLink fieldCode="EL" term="%22Higher+Education%22">Higher Education</searchLink><br /><searchLink fieldCode="EL" term="%22Postsecondary+Education%22">Postsecondary Education</searchLink>
– Name: Subject
  Label: Descriptors
  Group: Su
  Data: <searchLink fieldCode="DE" term="%22Science+Instruction%22">Science Instruction</searchLink><br /><searchLink fieldCode="DE" term="%22College+Science%22">College Science</searchLink><br /><searchLink fieldCode="DE" term="%22Undergraduate+Study%22">Undergraduate Study</searchLink><br /><searchLink fieldCode="DE" term="%22Organic+Chemistry%22">Organic Chemistry</searchLink><br /><searchLink fieldCode="DE" term="%22Scientific+Concepts%22">Scientific Concepts</searchLink><br /><searchLink fieldCode="DE" term="%22Science+Experiments%22">Science Experiments</searchLink><br /><searchLink fieldCode="DE" term="%22Science+Laboratories%22">Science Laboratories</searchLink><br /><searchLink fieldCode="DE" term="%22Laboratory+Experiments%22">Laboratory Experiments</searchLink>
– Name: DOI
  Label: DOI
  Group: ID
  Data: 10.1021/acs.jchemed.9b00872
– Name: ISSN
  Label: ISSN
  Group: ISSN
  Data: 0021-9584
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: An undergraduate organic chemistry experiment has been developed that features asymmetric synthesis of an enantioenriched secondary alcohol, followed by determination of its absolute configuration using the competing enantioselective conversion (CEC) method. Students are given a ketone and an unknown enantiomer of CBS (Corey-Bakshi-Shibata) catalyst. This reaction forms an enantioenriched secondary alcohol of unknown absolute configuration. Students then determine the absolute configuration via the CEC method. The CEC method is a modern application of the Horeau method that runs parallel reactions using both enantiomers of a chiral acyl-transfer catalyst, homobenzotetramisole (HBTM). Reactions are quenched concurrently, and reaction rates are compared using thin-layer chromatography (TLC) and/or [superscript 1]H nuclear magnetic resonance (NMR) spectroscopy to determine the fast and the slow reactions. By comparing the faster reaction to a previously determined mnemonic, the absolute configuration of the alcohol can be determined. From this information, students can then determine which enantiomer of CBS catalyst they used to form the enantioenriched alcohol. Both parts of this experiment were successfully completed in one 5 h lab section. This experiment provides an opportunity for discussion of important chemistry concepts including asymmetric synthesis, asymmetric catalysis, kinetic resolution, mechanism, transition state theory, and inert-atmosphere techniques.
– Name: AbstractInfo
  Label: Abstractor
  Group: Ab
  Data: As Provided
– Name: DateEntry
  Label: Entry Date
  Group: Date
  Data: 2020
– Name: AN
  Label: Accession Number
  Group: ID
  Data: EJ1248701
PLink https://search.ebscohost.com/login.aspx?direct=true&site=eds-live&db=eric&AN=EJ1248701
RecordInfo BibRecord:
  BibEntity:
    Identifiers:
      – Type: doi
        Value: 10.1021/acs.jchemed.9b00872
    Languages:
      – Text: English
    PhysicalDescription:
      Pagination:
        PageCount: 8
        StartPage: 793
    Subjects:
      – SubjectFull: Science Instruction
        Type: general
      – SubjectFull: College Science
        Type: general
      – SubjectFull: Undergraduate Study
        Type: general
      – SubjectFull: Organic Chemistry
        Type: general
      – SubjectFull: Scientific Concepts
        Type: general
      – SubjectFull: Science Experiments
        Type: general
      – SubjectFull: Science Laboratories
        Type: general
      – SubjectFull: Laboratory Experiments
        Type: general
    Titles:
      – TitleFull: Asymmetric Synthesis and Absolute Configuration Determination of an Enantioenriched Alcohol: A Discovery-Based Undergraduate Laboratory Experiment
        Type: main
  BibRelationships:
    HasContributorRelationships:
      – PersonEntity:
          Name:
            NameFull: King, Ryan P.
      – PersonEntity:
          Name:
            NameFull: Wagner, Alexander J.
      – PersonEntity:
          Name:
            NameFull: Burtea, Alexander
      – PersonEntity:
          Name:
            NameFull: King, Susan M.
    IsPartOfRelationships:
      – BibEntity:
          Dates:
            – D: 01
              M: 03
              Type: published
              Y: 2020
          Identifiers:
            – Type: issn-print
              Value: 0021-9584
          Numbering:
            – Type: volume
              Value: 97
            – Type: issue
              Value: 3
          Titles:
            – TitleFull: Journal of Chemical Education
              Type: main
ResultId 1