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2001
addition reactions
addition reactions
O 0060
Reaction of Benzyl Grignard Reagents with Trifluoroacetyldihydropy16 - 049 rans and Other Cyclic β-Alkoxy-α,β-unsaturated Trifluoromethylketones.
— Reaction of benzyl and allylic Grignard reagents (II), (VI) and
(VIII) with β-alkoxy-α,β-unsaturated trifluoromethyl ketones (I) and (XI)
proceeds by 1,2-addition to furnish allylic alcohols (III), (VII), (IX)/(X) and
(XII)/(XIII) in good yields. Interestingly, when the reaction of dihydropyranyl
ketone (I) with benzylmagnesium bromide (IIa) is carried out in the presence
of THF, the 1,4-addition products (IV) and (V) are obtained exclusively. The
addition reaction of benzylmagnesium bromide to dihydrofuranyl ketone (XIV)
proceeds less selectively and the 1,2-adduct (XV) is obtained as minor product
besides 1,4-adducts (XVI) and (XVII). In some cases, even spiroadduct (XVIII)
is formed in low amounts. — (COLES, SIMON J.; MELLOR, JOHN M.;
EL-SAGHEER, AFAF H.; SALEM, EZZ EL-DIN M.; METWALLY, REDA
N.; Tetrahedron 56 (2000) 51, 10057-10066; Dep. Chem., Univ. Southampton,
Southampton SO17 1BJ, UK; EN)
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