An aminocatalyzed stereoselective strategy for the formal alpha-propargylation of ketones

• Grant number: 17/09462-8
• Support Opportunities: Regular Research Grants - Publications - Scientific article
• Start date: July 01, 2017
• End date: December 31, 2017
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Igor Dias Jurberg
• Grantee: Igor Dias Jurberg
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
• Associated research grant: 15/20809-4 - Exploring the Chemistry of Isoxazol-5-ones as Versatile Building Blocks in Organic Synthesis, AP.R

Abstract

A two-step reaction sequence is described for the asymmetric formal alpha-propargylation of ketones. This approach takes advantage of an aminocatalyzed conjugate addition of ketones to alkylidene isoxazol-5-ones, followed by a controlled nitrosative degradation event. The target compounds can be accessed in broad scope, in moderate to good yields, perfect diastereocontrol and good to excellent enantioselectivities. (AU)