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Ruthenium(II)‐Catalyzed [2+2] Cycloadditions of anti 7‐Substituted Norbornenes
Author(s) -
Jordan Robert W.,
Le Marquand Paul,
Tam William
Publication year - 2008
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.200700706
Subject(s) - chemistry , alkyne , alkene , ruthenium , stereoselectivity , catalysis , reactivity (psychology) , medicinal chemistry , organic chemistry , medicine , alternative medicine , pathology
The ruthenium(II)‐catalyzed [2+2] cycloadditions of anti 7‐substituted norbornenes with an alkyne were investigated. The cycloadditions were found to proceed with a high degree of stereoselectivity, giving only the exo stereoisomers in moderate to good yields using an improved protocol. Comparative rate studies between a variety of anti 7‐substituted norbornenes and an alkyne revealed that the reactivity of the alkene component decreases dramatically as the alkene becomes more electron deficient.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)