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Rhodium(I)‐Catalyzed ‘Metallo‐Ene’ Cyclizations/β‐Eliminations
Author(s) -
Oppolzer Wolfgang,
Fürstner Alois
Publication year - 1993
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19930760618
Subject(s) - chemistry , catalysis , rhodium , yield (engineering) , ene reaction , medicinal chemistry , carbonate , ring (chemistry) , stereochemistry , organic chemistry , materials science , metallurgy
Octadienyl carbonates 5 provide cyclic 1,4‐dienes 6 when treated with Rh 1 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 Rh 1 catalysis but the trans ‐isomer 12 when catalyzed by Pd 0 . Azaoctadienyl carbonate 5a undergoes elimination with [RhH(PPh 3 ) 4 ] (5 mol‐%, 80°) in MeCN giving acyclic triene. 7 .