Item – Theses Canada

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OCLC number
1032952585
Link(s) to full text
LAC copy
LAC copy
Author
Hili, Ryan Matthew.
Title
Unprotected Amino Aldehydes in Organic Synthesis.
Degree
Ph. D. -- University of Toronto, 2010
Publisher
Toronto : University of Toronto, 2010.
Description
1 online resource
Notes
Includes bibliographical references.
Abstract
In 1908, H. Emil Fisher attempted to prepare glycinal, an unprotected amino aldehyde, which he found to be inherently unstable and prone to polymerization. This instability arises from the propensity of amines to condense with aldehydes. Accordingly, amino aldehydes require protection of the amine functional group. On the contrary, aziridines do not condense with aldehydes; the aziridine ring-strain precludes the formation of an iminium ion. Predicated upon this orthogonal reactivity, a stable class of unprotected amino aldehydes has been prepared, and an in-depth investigation into their chemical reactivity has been undertaken. Reactions designed to utilize both their nucleophilic (amine) and electrophilic (aldehyde) centres have demonstrated their capacity to forge multiple bonds in a single transformation, and have been implemented in the synthesis of complex heterocycles and cyclic peptides.
Other link(s)
hdl.handle.net
tspace.library.utoronto.ca
Subject
Amino aldehyde.
aziridine.
multicomponent.
domino reaction.
cyclic peptide.
macrocyclization.
amphoteric.
protecting group free.
0490.