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An Unprecedented Domino Double Allylsilane [3+2] Cycloaddition/Wagner–Meerwein Rearrangement/Friedel–Crafts Alkylation/Elimination Reaction Sequence Leading to a Novel Pentacyclic Ring System
Author(s) -
Knölker HansJoachim,
Baum Elke,
Graf Regina,
Jones Peter G.,
Spieß Oliver
Publication year - 1999
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19990903)38:17<2583::aid-anie2583>3.0.co;2-1
Subject(s) - stereocenter , cycloaddition , domino , chemistry , ring (chemistry) , sequence (biology) , lewis acids and bases , friedel–crafts reaction , conjugated system , stereoselectivity , stereochemistry , cascade reaction , organic chemistry , catalysis , enantioselective synthesis , biochemistry , polymer
A stereoselective synthesis of the disilyl derivatives 3 is achieved by the title reaction, an unprecedented Lewis acid promoted domino reaction, between the cross‐conjugated dienone 1 and the allylsilanes 2 . The configurations of the five stereogenic centers of this novel ring system are established in the first step of the reaction sequence, the double [3+2] cycloaddition.