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- W1545277708 abstract "Abstract Because of the great ease of preparation of allyl phenyl sulfides and their smooth reductive lithiation using lithium naphthalenide or 1-(dimethylamino)naphthalenide, these are ideal substrates for a particularly versatile preparative method for allylic anions. The lithio compounds react with aldehydes and ketones readily and with moderate regioselectivity. The allyltitanium compounds formed by addition of titanium tetraisopropoxide react with enals with very high regioselectivity and stereoselectivity. The allyltilanium compound derived from 2-phenylthio-1-methylenecyclohexane adds in a 1,2-fashion to crotonaldehyde at the secondary terminus of the allylic system. The potassium salt of this adduct undergoes the anion-accelerated oxy Cope rearrangement to the product of formal 1,4-addition of the crotonaldehyde to the primary terminus. The rearrangement product is an aldehyde which is also synthetically useful, undergoing the Lewis acid catalyzed ene reaction to produce a ring-closed product." @default.
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- W1545277708 date "1986-01-01" @default.
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- W1545277708 title "Reductive metallation" @default.
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- W1545277708 doi "https://doi.org/10.1016/s0040-4020(01)90569-1" @default.
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