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2005
Ketones
Q 0350
10- 073
MgI2-Catalyzed Halo Aldol Reaction: A Practical Approach to (E)-β-Iodovinyl−β'-hydroxyketones. — A novel halo aldol reaction via a tandem functionalization of
the 1,4-positions of α,β-acetylenic ketones is reported. In the first step of the synthesis
1-iodo-3-silyloxy-1,3-butadienes are generated by reacting Tms-I with unsaturated ketones (I) without the use of any catalyst. Subsequent halo aldol reaction of these intermediates with aldehydes catalyzed by MgI2 affords iodovinyl-hydroxyketones (III) in
good yield and exclusive E-selectivity. — (WEI, H.-X.; TIMMONS, C.; FARAG, M.
A.; PARE, P. W.; LI*, G.; Org. Biomol. Chem. 2 (2004) 20, 2893-2896; Dep. Chem.
Biochem., Tex. Tech. Univ., Lubbock, TX 79409, USA; Eng.) — Bartels
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