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2005
E/Z-Selectivity
O 0033
Application of Organocerium Reagents for the Efficient Conversion of Z-α,β-UnWeinreb Amides to Z-α,β-Unsaturated Ketones. — The reaction of
36- 034 saturated
Z-rich α,β-unsaturated Weinreb amides, such as (I), (V) and (VIII) with organolithium
and organocerium reagents are examined. Taking into consideration both the extent of
geometry retention and cleanness of the reaction, organocerium reagents are more effective for the conversion to Z-α,β- unsaturated ketones, e.g. (III)/(IV), (VI)/(VII) and
(IX)/(X). The required Z-rich α,β-unsaturated Weinreb amides (I), (V) and (VIII) are
prepared by the Wittig—Horner—Emmons reaction of phosphonic acid ester with
aldehydes in the presence of a suitable base. — (KOJIMA*, S.; HIDAKA, T.;
YAMAKAWA, A.; Chem. Lett. 34 (2005) 4, 470-471; Dep. Chem., Grad. Sch. Sci.,
Hiroshima Univ., Higashi-Hiroshima 739, Japan; Eng.) — M. Paetzel
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