1,2-Bisanionic Coupling Approach to 2,3-Disubstituted Cyclopentenols and Cyclopentenones
Marco Luparia, Alessandro Vadalà, Giuseppe Zanoni and Giovanni Vidari*
*Dipartimento di Chimica Organica, Università di Pavia, Via Taramelli 10,
27100 Pavia, Italy, Email: vidari
unipv.it
M. Luparia, A. Vadalà, G. Zanoni, G. Vidari, Org. Lett., 2006, 8, 2147-2150.
DOI: 10.1021/ol060654y
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Abstract
On exposure to BuLi, 3-bromo-2-iodocyclopent-2-enol O-TBS ether undergoes iodine-lithium permutation with complete regioselectivity. Reaction with different electrophiles affords the corresponding 2-substituted-3-bromocyclopentenol derivatives. Subsequent bromo-lithium exchange with t-BuLi, followed by reaction with an equal or different electrophile, affords 2,3-disubstituted cyclopentenols.
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Key Words
Coupling, Addition, Allylation
ID: J54-Y2006-1290
