2026-09-20T11:14:19Zhttps://dspace.mit.edu/server/oai/requestoai:dspace.mit.edu:1721.1/843782022-01-13T07:53:58Zcom_1721.1_7582com_1721.1_7581col_1721.1_131022
Rick L. Danheiser.
Tumidajski, Stephanie
Massachusetts Institute of Technology. Department of Chemistry.
Massachusetts Institute of Technology. Department of Chemistry
2014-01-23T18:40:05Z
2014-01-23T18:40:05Z
2013
2013
http://hdl.handle.net/1721.1/84378
867637595
Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2013.
Cataloged from PDF version of thesis.
Includes bibliographical references.
Iminoacetonitriles participate as activated imino dienophiles in intermolecular and intramolecular aza Diels-Alder reactions affording tetrahydropyridines and indolizidines. The [alpha]-amino nitrile cycloadducts are versatile synthetic intermediates that participate in a variety of stereoselective transformations to further elaborate the six-membered ring. This thesis describes the scope of the intermolecular [4 + 2] cycloaddition of N-benzyliminoacetonitrile with unactivated and activated dienes, as well as, the synthetic elaboration of the cycloadducts. This thesis also describes the worked performed to complete the total syntheses of indolizidines (-)- 235B', (-)-235B", and (+)-235B" using the aza Diels-Alder reaction of an iminoacetonitrile as the key step.
by Stephanie Tumidajski.
Ph.D.
372 pages
eng
Massachusetts Institute of Technology
M.I.T. theses are protected by
copyright. They may be viewed from this source for any purpose, but
reproduction or distribution in any format is prohibited without written
permission. See provided URL for inquiries about permission.
http://dspace.mit.edu/handle/1721.1/7582
Chemistry.
[4 + 2] cycloadditions of iminoacetonitriles : synthesis of highly substituted tetrahydropyridines and indolizidine alkaloids
Synthesis of highly substituted tetrahydropyridines and indolizidine alkaloids
Thesis
application/pdf
false
Publication
unknown
unknown
<Publication xmlns="https://www.openaire.eu/cerif-profile/1.1/" id="43d3584d-ea0c-4fae-b148-b5f365eddb6f">
<Type xmlns="https://www.openaire.eu/cerif-profile/vocab/COAR_Publication_Types">http://purl.org/coar/resource_type/c_1843</Type>
<Language>eng</Language>
<Title>[4 + 2] cycloadditions of iminoacetonitriles : synthesis of highly substituted tetrahydropyridines and indolizidine alkaloids</Title>
<Subtitle>Synthesis of highly substituted tetrahydropyridines and indolizidine alkaloids</Subtitle>
<PublishedIn>
<Publication>
</Publication>
</PublishedIn>
<PublicationDate>2013</PublicationDate>
<Authors>
<Author>
<DisplayName>Tumidajski, Stephanie</DisplayName>
<Affiliation>
<OrgUnit>
</OrgUnit>
</Affiliation>
</Author>
</Authors>
<Editors>
</Editors>
<Publishers>
<Publisher>
<DisplayName>Massachusetts Institute of Technology</DisplayName>
<OrgUnit />
</Publisher>
</Publishers>
<License>http://dspace.mit.edu/handle/1721.1/7582</License>
<Keyword>Chemistry.</Keyword>
<Abstract>Iminoacetonitriles participate as activated imino dienophiles in intermolecular and intramolecular aza Diels-Alder reactions affording tetrahydropyridines and indolizidines. The [alpha]-amino nitrile cycloadducts are versatile synthetic intermediates that participate in a variety of stereoselective transformations to further elaborate the six-membered ring. This thesis describes the scope of the intermolecular [4 + 2] cycloaddition of N-benzyliminoacetonitrile with unactivated and activated dienes, as well as, the synthetic elaboration of the cycloadducts. This thesis also describes the worked performed to complete the total syntheses of indolizidines (-)- 235B', (-)-235B", and (+)-235B" using the aza Diels-Alder reaction of an iminoacetonitrile as the key step.</Abstract>
<Access xmlns="http://purl.org/coar/access_right"
>
</Access>
</Publication>