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Lewis Acid Catalyzed Cyclizations of Epoxidized Baylis–Hillman Products: A Straightforward Synthesis of Octahydrobenzo[ e ]azulenes
Author(s) -
Konopacki Donald B.,
Shortsleeves Kelley C.,
Turnbull Mark M.,
Wikaira Jan L.,
Hobson Adrian D.
Publication year - 2015
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.201500452
Subject(s) - chemistry , catalysis , organic chemistry , lewis acids and bases , stereochemistry
Tricyclic keto‐diols have been synthesized from 2‐cyclopenten‐1‐one in a three‐step annulation procedure. The importance of aryl ring electronics and steric contributions and the choice of Lewis acid were investigated for the final cyclization step. An unexpected cyclization product was identified, suggesting multiple mechanisms for the cyclization process.