Type of Document Dissertation Author DeGuzman, Joseph Christopher URN etd-06192006-161356 Title Memory of Chirality in 1,4-Benzodiazepin-2-ones Degree PhD Department Chemistry Advisory Committee
Advisor Name Title Carlier, Paul R. Committee Chair Etzkorn, Felicia A. Committee Member Hanson, Brian E. Committee Member Kingston, David G. I. Committee Member Tanko, James M. Committee Member Keywords
- axial chirality
- Memory of chirality
- enantiomeric excess
- dynamic chirality
Date of Defense 2006-05-31 Availability unrestricted 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.
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