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Pt(II) or Ag(I) salt catalyzed cycloisomerizations and tandem cycloadditions forming functionalized azacyclic arrays

TitlePt(II) or Ag(I) salt catalyzed cycloisomerizations and tandem cycloadditions forming functionalized azacyclic arrays
Publication TypeJournal Article
Year of Publication2004
AuthorsHarrison, TJ, Dake, GR
JournalOrganic Letters
Volume6
Pagination5023-5026
Date PublishedDec
Type of ArticleArticle
ISBN Number1523-7060
KeywordsCOMPLEXES, cyclizations, ENAMIDES, ENANTIOSELECTIVE REACTIONS, ENYNES, ORGANIC-SYNTHESIS, palladium, platinum, REORGANIZATION, SKELETAL, STEREOCONTROLLED TOTAL-SYNTHESIS
Abstract

Cyclic ene-N-p-toluenesulfonamides tethered to an electron-deficient alkyne undergo cycloisomerizations readily under the influence of catalytic Pt(II) salts (PtCl2 or [dppbPtmu-OH](2)(BF4)(2)) or AgOTf. Yields for this process range from 47% to 99%. The resulting functionalized 2-azahydrindans can be reacted further using the Diels-Alder reaction. Tandem cycloisomerization-cycloaddition reactions in one pot generate highly functionalized 1-azadecalin ring systems in a highly stereocontrolled manner.

URL<Go to ISI>://000225812300057