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Convenient Synthesis of Heterobicycles by Domino Heck−Diels−Alder Reactions
Author(s) -
Bhat Laxminarayan,
Steinig Arno G.,
Appelbe Ruth,
de Meijere Armin
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200105)2001:9<1673::aid-ejoc1673>3.0.co;2-g
Subject(s) - chemistry , domino , intramolecular force , cycloaddition , palladium , yield (engineering) , diels–alder reaction , organic chemistry , catalysis , medicinal chemistry , materials science , metallurgy
Palladium(0)‐catalyzed intramolecular cross coupling of bromodialkenylamines, bromoalkenylalkenamides and bromodialkenyl ethers followed by in situ [4+2] cycloaddition with suitable dienophiles gave tetrahydroisoindolines (31−73% yield), tetrahydroisoindolin‐1‐ones (43−51%) and hexahydrobenzo[ c ]furans (35−55%), and hexahydro‐1 H ‐[2]pyrindines (66−75%), respectively, each in one‐pot operations.