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

โœ Scribed by Koji Takaku; Hiroshi Shinokubo; Koichiro Oshima

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
202 KB
Volume
39
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The reaction of l-triphenylsilyl-2-propenyllithium with ethylene oxide afforded an adduct, a lithium salt of 3-triphenylsilyl-4-penten-I-ol, which regenerated an allyllithium species, 3-1ithio-5triphenylsiloxy-l-pentene via anionic rearrangement ofa 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.

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