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Synthesis of Enantioenriched Heterocycles by Tandem Sakurai Allylation/Intramolecular Cyclization Processes

Citation

Ordner, Ciara Mary (2018) Synthesis of Enantioenriched Heterocycles by Tandem Sakurai Allylation/Intramolecular Cyclization Processes. Senior thesis (Major), California Institute of Technology. doi:10.7907/FHRD-3724. https://resolver.caltech.edu/CaltechTHESIS:10192018-145939043

Abstract

Organosilanes are advantageous in organic synthesis due to their ability to act as both stable products and reactive intermediates. A stereospecific one-pot cascade reaction that converts chiral allylic silanes into chiral heterocycles was developed using Lewis acid catalysis. We report on the development of this cascade reaction, optimization to benchtop- scale chemistry, and preliminary investigation into the synthetic scope. In our studies, we were successful in varying the cyclization ring size, investigating cyclization preference in the presence of multiple electrophilic leaving groups, and altering the functional groups present on the aldehyde starting material. Ultimately, we envision this method will be useful in the synthesis of a variety of enantioenriched heterocycles found in bioactive natural products, many of which have may find use as potential drug targets.

Item Type:Thesis (Senior thesis (Major))
Subject Keywords:tetrahydropyrans; tetrahydrofurans; heterocycle; Sakurai allylation
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Awards:Library Friends Senior Thesis Prize Finalist, 2018
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Reisman, Sarah E.
Group:Library Friends' Senior Thesis Prize
Thesis Committee:
  • None, None
Defense Date:8 June 2018
Funders:
Funding AgencyGrant Number
Richard H. Cox FellowshipUNSPECIFIED
John Stauffer FellowshipUNSPECIFIED
NIHUNSPECIFIED
Record Number:CaltechTHESIS:10192018-145939043
Persistent URL:https://resolver.caltech.edu/CaltechTHESIS:10192018-145939043
DOI:10.7907/FHRD-3724
ORCID:
AuthorORCID
Ordner, Ciara Mary0000-0002-6644-7863
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:11238
Collection:CaltechTHESIS
Deposited By: Ciara Ordner
Deposited On:24 Oct 2018 22:26
Last Modified:01 Feb 2021 22:45

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