2007•Organic LettersRequires access

Lewis Base Activation of Lewis Acids: Development of a Lewis Base Catalyzed Selenolactonization

Scott E. Denmark, William R. Collins

Abstract

The concept of Lewis base activation of Lewis acids has been applied to the selenolactonization reaction. Through the use of substoichiometric amounts of Lewis bases with "soft" donor atoms (S, Se, P) significant rate enhancements over the background reaction are seen. Preliminary mechanistic investigations have revealed the resting state of the catalyst as well as the significance of a weak Brønsted acid promoter.

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Key concepts: Lewis acids and bases, Chemistry, Catalysis, Base (topology), Brønsted–Lowry acid–base theory, Medicinal chemistry, Organic chemistry, Mathematics