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Construction of Bi‐ and Tricyclic Skeletons by Domino‐ Heck–Diels–Alder Reactions
Author(s) -
Körbe Stefanie,
de Meijere Armin,
Labahn Thomas
Publication year - 2002
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 - 10.1002/1522-2675(200210)85:10<3161::aid-hlca3161>3.0.co;2-2
Subject(s) - chemistry , yield (engineering) , intramolecular force , cycloaddition , tricyclic , iminium , domino , intermolecular force , derivative (finance) , lewis acids and bases , palladium , medicinal chemistry , intramolecular reaction , catalysis , organic chemistry , stereochemistry , molecule , materials science , economics , financial economics , metallurgy
Palladium‐catalyzed intramolecular reactions of 2‐bromo 1,6‐dienes followed by intermolecular [4+2] cycloaddition with suitable dienophiles in one‐pot operations gave hexahydroindenes 8 and 9 in yields of 40–78%, an hexahydro‐ s ‐indacene derivative 13 could be obtained in up to 25% yield with cyclopent‐2‐en‐1‐one ( 10 ) as a dienophile in the presence of different Lewis acids, and a spirocyclopentane‐hexahydroindenone 18 could be isolated in 72% yield. When in‐situ ‐formed iminium salts were used as heterodienophiles, hexahydro‐1 H ‐[2]pyrindinols 31 could be obtained in a one‐pot two‐step operation in 29–46% yield.