Presentation Title

Advancements in the Synthesis of BINOL-Derived Bisphosphrylimides

Faculty Mentor

Dr. Robert Iafe

Start Date

23-11-2019 10:15 AM

End Date

23-11-2019 10:30 AM

Location

Markstein 205

Session

oral 2

Type of Presentation

Oral Talk

Subject Area

physical_mathematical_sciences

Abstract

One of the most significant requirements in the application of bioactive catalysts in the pharmaceutical industry is their capability to provide enantioselective products. An effort in straying from metal-based catalysts while simultaneously providing success in enantioselectivity has become one of the many attempts made by chemists in promoting greener chemistry. Literature has demonstrated promise in the use of BINOL-derived catalysts for such reactions, with the asymmetric organocatalyst bisphosphorylimide providing results similar to those of traditional metal-based catalysts. It has been previously shown that enantioselective Friedel-Crafts reactions can be accomplished through the functionalization of bisphosphorylimides. Through the functionalization of bisphosphorylimide one is able to successfully build an environment that promotes acidity, electrophilicity, and enantioselectivity, all aspects that parallel chemical mechanisms that already exist in nature. The architecture of the bisphosphorylimide scaffold provides similar reactivity to that of the active site of an enzyme, allowing for the synthesis of enantioenriched products. In an attempt to develop novel synthesis of a bisphosphorylimide catalyst, an improvised protection of the hydroxyl groups of BINOL was accomplished via benzyl chloromethyl ether. Doing so, the first intermediate of the multistep reaction scheme for a functionalized bisphosphorylimide was successfully synthesized when substituting reagents from a traditionally used method. Upon synthesis the resulting product was characterized via thin layer chromatography Rfcomparison and 1H-NMR spectroscopy.

This document is currently not available here.

Share

COinS
 
Nov 23rd, 10:15 AM Nov 23rd, 10:30 AM

Advancements in the Synthesis of BINOL-Derived Bisphosphrylimides

Markstein 205

One of the most significant requirements in the application of bioactive catalysts in the pharmaceutical industry is their capability to provide enantioselective products. An effort in straying from metal-based catalysts while simultaneously providing success in enantioselectivity has become one of the many attempts made by chemists in promoting greener chemistry. Literature has demonstrated promise in the use of BINOL-derived catalysts for such reactions, with the asymmetric organocatalyst bisphosphorylimide providing results similar to those of traditional metal-based catalysts. It has been previously shown that enantioselective Friedel-Crafts reactions can be accomplished through the functionalization of bisphosphorylimides. Through the functionalization of bisphosphorylimide one is able to successfully build an environment that promotes acidity, electrophilicity, and enantioselectivity, all aspects that parallel chemical mechanisms that already exist in nature. The architecture of the bisphosphorylimide scaffold provides similar reactivity to that of the active site of an enzyme, allowing for the synthesis of enantioenriched products. In an attempt to develop novel synthesis of a bisphosphorylimide catalyst, an improvised protection of the hydroxyl groups of BINOL was accomplished via benzyl chloromethyl ether. Doing so, the first intermediate of the multistep reaction scheme for a functionalized bisphosphorylimide was successfully synthesized when substituting reagents from a traditionally used method. Upon synthesis the resulting product was characterized via thin layer chromatography Rfcomparison and 1H-NMR spectroscopy.