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Enantioselective Synthesis of Functionalized 1,5‐Cyclononadienes by Intramolecular Cycloalkylation under α , α ′‐Diallyl Coupling
Author(s) -
Deiters Alexander,
Fröhlich Roland,
Hoppe Dieter
Publication year - 2000
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 - 10.1002/1521-3773(20000616)39:12<2105::aid-anie2105>3.0.co;2-x
Subject(s) - intramolecular force , yield (engineering) , enantioselective synthesis , deprotonation , chemistry , stereochemistry , coupling (piping) , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , materials science , ion , metallurgy
Monocarbocyclic nine‐membered rings can be enantioselectively accessed by deprotonation of ( Z , Z )‐dienyl carbamates 1 and subsequent intramolecular α , α ′‐coupling to furnish the cyclononadienols 2 (R=H: 73% yield, e.r.=96:4; R=OSiPh 2 t Bu: 79% yield, e.r.=100:0, d.r.=94:6). Cby=2,2,4,4‐Tetramethyl‐1,3‐oxazolidin‐3‐ylcarbonyl, Cb=diisopropylaminocarbonyl.