Heteroaromatic synthesis via olefin cross-metathesis: entry to polysubstituted pyridines.

Journal article

The olefin cross-metathesis reaction provides a rapid and efficient method for the synthesis of α,β-unsaturated 1,5-dicarbonyl derivatives which then serve as effective precursors to mono-tetrasubstituted pyridines. Manipulation of the key 1,5-dicarbonyl intermediate allows access to pyridines with a wide range of substitution patterns. An extension of this methodology facilitates the preparation of pyridines embedded within macrocycles, as exemplified by an efficient synthesis of (R)-(+)-muscopyridine. High levels of regiocontrol, short reaction sequences, and facile substituent variation are all notable aspects of this methodology.

Authors: Donohoe, T; Basutto, J; Bower, J; Rathi, A

• Publication status: Published
• Journal: Organic letters
• Volume: 13
• Issue: 5
• Pages: 1036-1039
• Publication date: 2011-03-01
• DOI: 10.1021/ol103088r
• EISSN: 1523-7052
• ISSN: 1523-7060
• Language: English
• Keywords: Alkenes; Pyridines; Catalysis; Molecular Structure; Stereoisomerism