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Synthesis of Bicyclic Ethers by a Gold/Palladium/Gold‐Catalyzed Cyclization/Cross Coupling Sequence
Author(s) -
Gockel Birgit,
Krause Norbert
Publication year - 2010
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/ejoc.200901010
Subject(s) - chemistry , palladium , catalysis , yield (engineering) , stereoselectivity , bicyclic molecule , combinatorial chemistry , coupling reaction , surface modification , coupling (piping) , organic chemistry , materials science , metallurgy , mechanical engineering , engineering
The stereoselective gold‐catalyzed 6‐ endo cyclization ofvarious β‐hydroxyallenes in the presence of N ‐iodosuccinimide affords iodinated dihydropyrans in good yield. Subsequent functionalization by palladium‐catalyzed cross coupling opens an access to α‐hydroxyallenes that are converted in a second gold‐catalyzed cyclization into furopyrans which occur in various natural products.