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Chasing Enantioselectivity – Synthesis of Chiral α-Quaternary Carboxylic Acid Building Blocks

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Date Issued:
2017
Summary:
The advancements being made every day in drug discovery research are pushing the boundaries of synthesis methods that have already been developed, driving chemists to discover new reactions and methods to meet the demand. Two areas that have received much attention are the incorporation of halogens to complex molecules, and the induction of chirality on quaternary carbons. Halogenated drugs, particularly fluorinated compounds, are becoming increasingly medicinally important as pharmaceutical companies aim to give their products improvements in metabolic stability, target binding, and transport properties, making new methods for selectively installing halogens of the utmost important. We recently began developing a method to create a carboxylic acid with a chiral α-quaternary center containing fluorine or bromine by asymmetric halogenation. This research also seeks to elucidate the specific mechanism by which our reactions induce chirality, thereby providing the basis upon which to make improvements in yield, enantioselectivity, and scope. Our results and progress toward a more universally applicable method will be discussed.
Title: Chasing Enantioselectivity – Synthesis of Chiral α-Quaternary Carboxylic Acid Building Blocks.
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Name(s): Barth, Emily, author
FGCU Research Day
Type of Resource: text
Issuance: single unit
Date Issued: 2017
Physical Form: PDF
Language(s): English
eng
Summary: The advancements being made every day in drug discovery research are pushing the boundaries of synthesis methods that have already been developed, driving chemists to discover new reactions and methods to meet the demand. Two areas that have received much attention are the incorporation of halogens to complex molecules, and the induction of chirality on quaternary carbons. Halogenated drugs, particularly fluorinated compounds, are becoming increasingly medicinally important as pharmaceutical companies aim to give their products improvements in metabolic stability, target binding, and transport properties, making new methods for selectively installing halogens of the utmost important. We recently began developing a method to create a carboxylic acid with a chiral α-quaternary center containing fluorine or bromine by asymmetric halogenation. This research also seeks to elucidate the specific mechanism by which our reactions induce chirality, thereby providing the basis upon which to make improvements in yield, enantioselectivity, and scope. Our results and progress toward a more universally applicable method will be discussed.
Identifier: fgcu_UGR_0012 (IID)
Note(s): Poster from the Spring 2017 Research Day. Research Mentor: Dr. Daniel Paull.
Subject(s): asymmetric
enantioselectivity
chiral
Catalysis.
Fluorination.
Persistent Link to This Record: http://purl.flvc.org/fgcu/fd/fgcu_UGR_0012
Use and Reproduction: In Copyright - Educational Use Permitted In Copyright - Educational Use Permitted
Owner Institution: FGCU

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