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2005
C-C bond formation
O 0282
Carbon—Carbon Bond Formation by Radical Addition—Fragmentation Reacof O-Alkylated Enols. — O-tert-Alkyl enols such as (I) or (IV) undergo a variety
05- 047 tions
of C—C bond forming reactions with organic halides to give the radical adducts (III)
or (VI). The O-silylated ketene acetals (VII) or (XII) undergo reactions with organic
halides to give the adducts (IX), (XI) and (XIII) or with electron-poor alkenes to give
adducts such as (XVI) and (XVIII). The formation of the sole anti-product (XVIII)
(95% ds. of the crude reaction mixture) derived from both fumarate (XVII) and maleate
(XIX) is explained by a conformational equilibrium before the addition step. — (CAI,
Y.; ROBERTS*, B. P.; TOCHER, D. A.; BARNETT, S. A.; Org. Biomol. Chem. 2
(2004) 17, 2517-2529; Christopher Ingold Lab., Dep. Chem., Univ. Coll., London
WC1H 0AJ, UK; Eng.) — Kieslich
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