Skip to main content
Skip to main menu Skip to spotlight region Skip to secondary region Skip to UGA region Skip to Tertiary region Skip to Quaternary region Skip to unit footer


Stereoselective Synthesis and Applications of Sulfonylcyclopropanols as Modular Cyclopropanone and Homoenolate Equivalents

Prof. Vincent Lindsay, speaker
Prof. Vincent Lindsay
Assistant Professor, Department of Chemistry
North Carolina State University
Chemistry Building, Room 400
Organic Seminar

Cyclopropanone derivatives have long been regarded as unusable and elusive synthetic intermediates, mainly owing to their prominent ring strain and kinetic instability. In this work, we report the enantioselective synthesis of sulfonylcyclopropanols, shown to be modular and versatile synthetic equivalents of the corresponding cyclopropanone derivatives. These reagents were found to smoothly react in a variety of reaction manifolds, including organometallic 1,2-addition affording cyclopropanols, nitrene chemistry to access chiral β-lactams, nickel-catalyzed C–C activation to cyclopentenones, as well as olefination chemistry as a general platform to chiral alkylidenecyclopropanes and other substituted cyclopropanes. Moreover, we have shown that these sulfonylcyclopropanols can also behave as ‘electrophilic homoenolate’ equivalents, effectively acting as ring-opened 2- or 3-carbon linchpin reagents depending on the reaction conditions. This work constitutes the first general enantioselective route to cyclopropanone equivalents, thus unlocking a number of novel synthetic disconnections relevant to a variety of chemical industries.

Support Us

We appreciate your financial support. Your gift is important to us and helps support critical opportunities for students and faculty alike, including lectures, travel support, and any number of educational events that augment the classroom experience. Click here to learn more about giving.

Every dollar given has a direct impact upon our students and faculty.

Got More Questions?

Undergraduate inquiries: 

Registration and credit

AP Credit, Section Changes, Overrides,

Graduate inquiries:

Contact Us!

Assistant to the Department Head: Donna Spotts, 706-542-1919 

Main office phone: 706-542-1919 

Main Email:

Head of Chemistry: Prof. Jason Locklin