Abstract
Abstract The reaction of 1-triphenylsilyl-2-propenyllithium with ethylene oxide afforded an adduct, a lithium salt of 3-triphenylsilyl-4-penten-1-ol, which regenerated an allyllithium species, 3-lithio-5-triphenylsiloxy-1-pentene via anionic rearrangement of a silyl group from carbon to oxide in the presence of HMPA. This allylic lithium compound could be trapped in one-pot by various electrophiles to provide the corresponding adducts as regioisomeric mixtures. A successive addition of epoxides, aldehydes, and HMPA to 1,3-bis(triphenylsilyl)-2-propenyllithium gave 1,4-diol monosilylethers in one-pot with high regioselectivity.
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