[4 + 2] cycloadditions of iminoacetonitriles : synthesis of highly substituted tetrahydropyridines and indolizidine alkaloids
Name
867637595-MIT.pdf
Description
Full printable version
Size
22.99 MB
Format
Adobe PDF
Checksum (MD5)
fd28f77cc397a3e6ea122c0b9014797d
Author(s)
Tumidajski, Stephanie
Advisor(s)
Rick L. Danheiser.
Alternative Title
Synthesis of highly substituted tetrahydropyridines and indolizidine alkaloids
Date Issued
2013
Publisher
Massachusetts Institute of Technology
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.
Description
Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2013.
Cataloged from PDF version of thesis.
Includes bibliographical references.
Subjects
Chemistry.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
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.
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.
Persistent DSpace Link
