Palladium catalysed tandem cyclisation-anion capture. Part 5: Cascade hydrostannylation-bis-cyclisation-intramolecular anion capture. Synthesis of bridged- and spiro-cyclic small and macrocyclic heterocycles

Authors
Casaschi, A Grigg, R Sansano, JM Wilson, D Redpath, J
Citation
A. Casaschi et al., Palladium catalysed tandem cyclisation-anion capture. Part 5: Cascade hydrostannylation-bis-cyclisation-intramolecular anion capture. Synthesis of bridged- and spiro-cyclic small and macrocyclic heterocycles, TETRAHEDRON, 56(38), 2000, pp. 7541-7551
Citations number
35
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
38
Year of publication
2000
Pages
7541 - 7551
Database
ISI
SICI code
0040-4020(20000915)56:38<7541:PCTCCP>2.0.ZU;2-T
Abstract
A series of O- and N-alpha,omega-enyne derivatives of 2-iodoarylethers and 2-iodoarylamides undergo palladium catalysed cascade hydrostannylation of t he omega-alkyne moiety at 0-25 degrees C followed by bis-cyclisation at 100 -110 degrees C terminating in intramolecular sp(3)-sp(2) Stille coupling. T hese cascades provide a wide range of 5/6 and 5/12-17 membered bicyclic spi ro- and bridged-ring heterocycles. (C) 2000 Elsevier Science Ltd. All right s reserved.