References
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- The metal-halogen exchange reaction is a well-known method for preparing organolithium compounds: Wakefield, B. J. In Organolithium Methods; Academic: London, 1988; pp 21–52.
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- Suzuki , K. , Hasegawa , T. , Imai , T. , Maeta , H. and Ohta , S. 1995 . Tetrahedron , 51 : 4483 – 4494 . However, coupling with an α,β-epoxy aldehyde proved to be problematic in our hands. Direct addition of the resulting vinylzirconocene chloride intermediate to aldehydes is known to take place readily in the presence of AgAsF6 or AgClO4
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- For example, sequential treatment of 1c with tert-BuLi (2 equiv), MgBr2, and aldehyde 6 afforded, in good yield, the desired adduct 7, which was converted to the bis(tetrahydrofuran) subunit 8 of asteltoxin: Kim H. Cha J. K. unpublished results.1