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Preparation of Oxocanes by Electrophilic Cyclizations of Unsaturated Alcohols in the Presence of Bis(collidine)halonium( I ) Hexafluorophosphates
Author(s) -
Mendès Christelle,
Renard Sylvie,
Rofoo Mazin,
Roux MarieClaude,
Rousseau Gérard
Publication year - 2003
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.200390080
Subject(s) - cyclopropane , chemistry , electrophile , substituent , moiety , epoxide , tetrahydropyran , ring (chemistry) , dioxolane , derivative (finance) , medicinal chemistry , stereochemistry , organic chemistry , catalysis , financial economics , economics
7‐Octen‐1‐ols substituted in the sp 3 −sp 3 carbon chain with carbocyclic (phenyl and cyclopropane) and heterocyclic (epoxide and dioxolane) moieties were prepared and their cyclizations in the presence of bis(collidine)iodonium( I ) and ‐bromonium( I ) hexafluorophosphates as electrophiles were studied. Oxocanes were obtained in modest to good yields when a rigid cyclic moiety (cyclopropane or phenyl) was present in the chain, while yields of cyclizations were lower if the cyclic component had a certain flexibility (dioxolane). Low yields were obtained with substrates bearing an epoxide substituent, probably because of stability problems due to the presence of collidine. With the vinylcyclopropane alcohol 12 we observed mainly the opening of the cyclopropane ring and the cyclization produced a tetrahydropyran derivative. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)