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Enantioselective Syntheses of Cyclopentanoid Compounds from Isoprene and trans ‐1,3‐Pentadiene
Author(s) -
Baldenius Kai.U.,
tom Dieck Heindirk,
König Wilfried A.,
Icheln Detlef,
Runge Torsten
Publication year - 1992
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199203051
Subject(s) - isoprene , chemistry , acetic anhydride , enantioselective synthesis , yield (engineering) , organic chemistry , catalysis , octane , bicyclic molecule , acetic acid , copolymer , polymer , materials science , metallurgy
In only two steps, optically active 2 can be prepared from the basic chemicals isoprene, trans ‐l,3‐pentadiene, and acetic anhydride. A chiral diazadiene–iron complex catalyzes the codimerization of isoprene and trans ‐1,3‐pentadiene to 1 with regio‐ and enantioselectivity (89% yield, 61% ee ). In turn, 1 rearranges diastereoselectively to 2 and other bicyclo[3.3.0]octane derivatives under acid catalysis.