Abstract
dc:description.abstractMemory of chirality (MOC) is an emerging strategy in asymmetric synthesis. It has been applied to enolate chemistry, reactions involving carbocation intermediates, and to radical systems. In this strategy the chirality of an enantiopure reactant is transferred to the dynamic chirality of a reactive intermediate to produce stereospecific product. 1,4-Benzodiazepin-2-ones have been described as a "privileged" structure in medicinal chemistry. In addition to their uses as anxiolytics (Valium ®) and anti-epileptic agents (Clonopin ®), they have shown activity as HIV Tat antagonist, ras farnesyltransferase inhibitors in cancer cells, and antiarrhythmic agents. Because of the utility of this scaffold in the area of medicinal chemistry, it has served as a template in libraries for tens of thousands of compounds. Despite the vast diversity of 1,4-benzodiazepin-2-ones, there are few routes to enantiomerically enriched 3,3-disubstituted benzodiazepines containing a "quaternary" stereogenic center. This research will discuss the stereochemical properties of 1,4-benzodiazepin-2-ones, and provide a novel approach to synthesize enantiomerically enriched "quaternary" benzodiazepines with stereogenic centers through MOC, without the use of external chiral sources.
Degree
thesis:*- Name thesis:degree_name
- Ph. D.
- Level thesis:degree_level
- doctoral
- Discipline thesis:degree_discipline
- Chemistry
- Department dc:contributor.department
- Chemistry
- Grantor dc:publisher
- Virginia Tech
- Year dc:date.issued
- 2006
Author and committee
dc:creator, dc:contributor.*- Author dc:creator
-
- DeGuzman, Joseph Christopher
- Chair dc:contributor.committeechair
-
- Carlier, Paul R.
- Committee members dc:contributor.committeemember
-
- Tanko, James M.
- Kingston, David G. I.
- Hanson, Brian E.
- Etzkorn, Felicia A.
Subjects
dc:subject × 9Rights
dc:rights- Statement dc:rights
-
- In Copyright
- Licence dc:rights.uri
Identifiers
dc:identifier.*- Dc Identifier Other
- etd-06192006-161356
- OAI identifier oai:identifier
- oai:vtechworks.lib.vt.edu:10919/28079