Title page for ETD etd-06192006-161356

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
  • enolate
  • axial chirality
  • quaternary
  • racemization
  • benzodiazepine
  • conformer
  • Memory of chirality
  • enantiomeric excess
  • dynamic chirality
Date of Defense 2006-05-31
Availability unrestricted
Memory 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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