Distinguished Alumni Lecture - Seung Wook Kim

The Organic Seminar Series presents: Seung Wook Kim
Distinguished Alumni Lecture
Bristol Myers Squibb
Host: Mike Krische
Title: Hydrogen Borrowing and Beyond: A Journey from Iridium to Manganese Catalysis in Scalable Chiral Tetralol Synthesis
Refreshments served at 3:15pm
Location: WEL 2.122

Transition metal-catalyzed hydrogen auto transfer has been highlighted in organic chemistry as a result of its efficiency, low cost, and versatility. It enables the efficient formation of C-N and C-C bonds through non-activated alcohols. Recently, alcohol mediated hydrogen borrowing alkylation with commercially available iridium catalyst was developed and executed for a clinical campaign to produce 70kg of the desired intermediate towards an active pharmaceutical ingredient (API) in our portfolio. To develop a more economic and ecological process, we evaluated non-precious metals to mediate the desired transformation for future supply. Among early transition metals, manganese-catalyzed alkylation with the same substrate provided excellent reactivity and comparable purity at a significantly lower cost with a commercially available pre-catalyst and ligand. This presentation will cover catalyst selection, activation, and process development for this Mn-catalyzed transformation.