Re-visiting the diastereoselectivity of organocatalytic conjugate addition of 2-trimethylsiloxyfuran to trans-crotonaldehyde. (25th May 2021)

• Record Type: Journal Article
• Authors: Li, Liubo; El Khoury, Anton; Clement, Brennan O.; Harran, Patrick G.
• Is Part Of: Tetrahedron letters. Volume 72(2021)
• Publication Date: 2021-05-25
• Subjects: Mukaiyama-Michael reaction -- Butenolide; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2021.153056
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Conjugate addition sof 2-siloxyfuran to crotonaldehyde affords isomeric butenolides. Chiral imidazolidinone catalysis affords the ' anti ' isomer with moderate selectivity. Chiral prolinol catalysis generates the ' syn ' isomer with high dr and ee . Abstract: We describe the re-assignment of configuration previously ascribed to product diastereomers resultant from imidazolidinone-catalyzed conjugate addition of 2-trimethylsiloxyfuran to trans -crotonaldehyde. A modified procedure that uses a diphenylprolinol catalyst was subsequently developed to selectively provide the ' syn ' diastereomeric product in high enantiomeric excess on decagram scales.