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2005
Dioxane derivatives
R 0470
Phosphine-Catalyzed Synthesis of 1,3-Dioxan-4-ylidenes. — The reaction of allewith aldehydes affords (2,6-diaryl-[1,3]dioxan-4-ylidene)-acetates. The latter
33- 163 noates
are formed in excellent to moderate yields with complete diastereoselectivity and high
E/Z selectivities. The best results are obtained when PMe3 is used as a catalyst. Acid-mediated hydrolysis of the dioxane acetals leads to δ-hydroxy-β-ketoesters. The combination of neutral phosphine catalysis and acid hydrolysis provides an alternative for
the construction of ubiquitous ketoesters. — (ZHU, X.-F.; HENRY, C. E.; WANG, J.;
DUDDING, T.; KWON*, O.; Org. Lett. 7 (2005) 7, 1387-1390; Dep. Chem.
Biochem., Univ. Calif., Los Angeles, CA 90095, USA; Eng.) — R. Steudel
2005
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