One-pot synthesis of heterocyclic compounds initiated by chemoselective addition to β-acyl substituted unsaturated aldehydes with nucleophilic tin complexes

• Published in: Journal of organometallic chemistry Vol. 692; no. 1; pp. 604 - 619
• Main Authors: Shibata, Ikuya, Kato, Hirofumi, Yasuda, Makoto, Baba, Akio
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 2007
• Subjects: Allylation; Allylic tin; Heterocycle; Reduction; Reductive amination; Tin hydride; Reductive amination; Reduction; Heterocycle; Tin hydride; Allylic tin; Allylation
• ISSN: 0022-328X; 1872-8561
• DOI: 10.1016/j.jorganchem.2006.03.043

Various heterocyclic compounds such as 2-monosubstituted pyrroles, oxazolidones were prepared by chemoselective addition of nucleophilic tin complexes to β-acyl substituted unsaturated aldehydes in an one-pot procedure. β-Acyl substituted unsaturated aldehydes 1 were revealed to be good precursors for the synthesis of various heterocyclic compounds by the combination with tin nucleophiles. Various 2-monosubstituted pyrroles were prepared in an one-pot procedure via the reductive amination of formyl groups of 1 by using Bu 2SnIH–HMPA complex. One-pot synthesis of heterocycles was carried out initiated by chemoselective reduction of 1 with Bu 3SnH–HMPA complex and the subsequent reaction with heterocumulenes. Furthermore, the one-pot synthesis of nitrogen heterocyclic compounds accompanying chemo-, regio- and diastereoselective carbon–carbon bond formation in side chain moieties was effectively accomplished initiated by the regio- and diastereoselective allylation of the formyl group of 1 with allylic tin species.