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Journal Article

Rhodium(I)-Catalyzed 'Metallo-Ene' Cyclizations/β-Eliminations

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Oppolzer, W., & Fürstner, A. (1993). Rhodium(I)-Catalyzed 'Metallo-Ene' Cyclizations/β-Eliminations. Helvetica Chimica Acta, 76(6), 2329-2337. doi:10.1002/hlca.19930760618.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-A48D-B
Abstract
Octadienyl carbonates 5 provide cyclic 1,4-dienes 6 when treated with RhI complexes (1–10 mol-%) at 80°. Similar cyclization of cyclohexenyl acetate 8 affords cis- fused hexahydroindene 9. Analogous ring closures of nonadienyl carbonate 10 yield preferably the cis-divinypyrrolidine 11 with RhI catalysis but the trans-isomer 12 when catalyzed by Pd0. Azaoctadienyl carbonate 5a undergoes elimination with [RhH(PPh3)4] (5 mol-%, 80°) in MeCN giving acyclic triene 7.