Sequential carbon-carbon bond formation reaction using 1-silyl-2- propenyllithium

Article abstract of DOI:10.1016/S0040-4039(98)00271-8

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 onepot with high regioselectivity.