Title of Research Project
Synthesis of Sultams from Vinyl Aziridines and 1,4-Diazabicyclo[2.2.2]octane bis(sulfur dioxide)
Major
Chemistry
Research Abstract
Sultams are an important functional group found in medicinal compounds with anticancer and enzyme inhibition activity. Traditional methods for sultam synthesis often require harsh conditions and have limited substrate scope. This research focuses on developing a novel methodology for the production of sultams using DABSO (1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide)) and vinylic aziridines. Our synthetic strategy starts with a Corey-Chaykovsky epoxidation of cinnamaldehyde, followed by an epoxide-opening using sodium azide. The final vinylic aziridine is synthesized by mesylation and Staudinger reduction of the resulting azido alcohol. Reaction of this vinyl aziridine with DABSO may provide a new strategy for synthesizing sultams. Following this strategy, we have thus far synthesized the penultimate mesylate in 17% yield over 3 steps.
Faculty Mentor/Advisor
Herman Nikolayevskiy
Included in
Synthesis of Sultams from Vinyl Aziridines and 1,4-Diazabicyclo[2.2.2]octane bis(sulfur dioxide)
Sultams are an important functional group found in medicinal compounds with anticancer and enzyme inhibition activity. Traditional methods for sultam synthesis often require harsh conditions and have limited substrate scope. This research focuses on developing a novel methodology for the production of sultams using DABSO (1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide)) and vinylic aziridines. Our synthetic strategy starts with a Corey-Chaykovsky epoxidation of cinnamaldehyde, followed by an epoxide-opening using sodium azide. The final vinylic aziridine is synthesized by mesylation and Staudinger reduction of the resulting azido alcohol. Reaction of this vinyl aziridine with DABSO may provide a new strategy for synthesizing sultams. Following this strategy, we have thus far synthesized the penultimate mesylate in 17% yield over 3 steps.
