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Reactivity of the TMM Entity in the Cyclopentene Series − Observation of a Reversed Regioselectivity in Palladium‐Catalyzed [3+2] Cycloadditions
Author(s) -
Romero Juan Manuel López,
Sapmaz Selma,
Fensterbank Louis,
Malacria Max
Publication year - 2001
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 - 10.1002/1099-0690(200102)2001:4<767::aid-ejoc767>3.0.co;2-v
Subject(s) - regioselectivity , chemistry , cyclopentene , palladium , olefin fiber , reactivity (psychology) , catalysis , cycloaddition , ring (chemistry) , stereochemistry , organic chemistry , medicinal chemistry , medicine , alternative medicine , pathology
The first examples of palladium(0)‐catalyzed [3+2] cycloadditions involving an electron‐deficient olefin and a TMM entity incorporated into a five‐membered ring are described. In the case of gem ‐dimethyl precursor 7b , the regioselectivity is completely reversed, compared to that traditionally observed in these reactions (products 12M and 12m ). Additional results and an interpretation of these findings are given.