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1,2-Bisanionic Coupling Approach to 2,3-Disubstituted Cyclopentenols and Cyclopentenones

Marco Luparia, Alessandro VadalÓ, Giuseppe Zanoni and Giovanni Vidari*

*Dipartimento di Chimica Organica, UniversitÓ di Pavia, Via Taramelli 10, 27100 Pavia, Italy, Email:

M. Luparia, A. VadalÓ, G. Zanoni, G. Vidari, Org. Lett., 2006, 8, 2147-2150.

DOI: 10.1021/ol060654y

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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