Details

Autor(en) / Beteiligte

• Wender, Paul A.
• Husfeld, Craig O.
• Langkopf, Elke
• Love, Jennifer A.
• Pleuss, Norbert

Titel

The first metal-catalyzed intramolecular [5+2] cycloadditions of vinylcyclopropanes and alkenes: Scope, stereochemistry, and asymmetric catalysis

Ist Teil von

• Tetrahedron, 1998-06, Vol.54 (25), p.7203-7220

Ort / Verlag

Elsevier Ltd

Erscheinungsjahr

1998

Quelle

EZB-NALI5-00465 Elsevier Archive NL

Beschreibungen/Notizen

• The first studies of the metal-catalyzed [5+2] cycloadditions of vinylcyclopropanes and alkenes are described. These reactions proceed with exceptional diastereoselectivity and in good to excellent yields. The effect of tether and substituent variations are examined. In addition, preliminary studies show that enantioselective cycloadditions can be achieved through the use of catalysts modified with chiral phosphine ligands. This novel, general, and efficient procedure provides a fundamentally new approach to the synthesis of a variety of products of structural and medicinal significance. The first studies of the Rh(I)-catalyzed intramolecular [5+2] cycloaddition of alkenes and vinylcyclopropanes are described. The effects of tether and substituent variations in these high-yielding and exceptionally selective reactions are examined. Additionally, the preliminary investigation of catalysts modified with chiral ligands is discussed.