Dissertation/Thesis Abstract

Preparation of enantioenriched polyols and polyol amines and multiplying the catalytic output of reactions
by Kaviani Joupari, Makan, M.S., California State University, Long Beach, 2014, 159; 1527964
Abstract (Summary)

The preparation of enantiopure building blocks is a fundamental area of importance for synthetic chemistry. We became particularly interested in asymmetric ring opening of sylilcyclopentene oxides with different nucleophiles such as azide and acetate using Jacobsen's catalysts. Silylcyclopentene oxide is amenable to several distinct asymmetric catalytic transformations providing access to enantio-enriched tetraol triol-azide and triol-amines. The sequences employed allow for selective protection of one amine or alcohol from the four heteroatoms that are introduced into the carbon scaffold. We have now turned our attention towards utilizing bifunctional substrates containing two cyclopentene oxide rings as an attempt to double the molar output of these reactions, while reducing the waste created by spectator ligands. It turns out that the two asymmetric transformations work independent of the other functional groups present on the substrate and high enantioselectivity and good yield was achieved. This type of atom economy has other applications to multiplying catalytic output using other polyfunctional substrates.

Indexing (document details)
Advisor: Schramm, Michael P.
Commitee: Buonora, Paul T., Marinez, Eric R.
School: California State University, Long Beach
Department: Chemistry and Biochemistry
School Location: United States -- California
Source: MAI 53/01M(E), Masters Abstracts International
Subjects: Chemistry
Keywords: Asymmetric synthesis, Chiral polyol amines, Medicinal chemistry
Publication Number: 1527964
ISBN: 978-1-303-98488-4
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