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Nd(OTf) 3 ‐Catalyzed Cascade Reactions of Vinylidenecyclopropanes with Enynol: A New Method for the Construction of the 5–7–6 Tricyclic Framework and Its Scope and Limitations
Author(s) -
Yao LiangFeng,
Shi Min
Publication year - 2009
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.200900660
Subject(s) - chemistry , tricyclic , cyclopentane , catalysis , scope (computer science) , yield (engineering) , lewis acids and bases , enol , combinatorial chemistry , cascade reaction , organic chemistry , materials science , computer science , metallurgy , programming language
We report in this paper a Lewis acid [Nd(OTf) 3 ]‐catalyzed protocol to construct compounds containing a 5–7–6 tricyclic framework in good yield from readily accessible starting materials vinylidenecyclopropanes (VDCPs) 1 and enynols 2a – c under mild conditions. Upon examination of the scope and limitations of this reaction, it was found that the corresponding highly functionalized cyclopentane derivatives could be formed in good yields from the reaction VDCPs 1 and enol 2e or dienol 2c under identical conditions.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)