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2005
Oxazole derivatives
R 0220
Silver(I)-Promoted Asymmetric Halohydrin Reaction of Chiral N-Enoyl-2-oxazoScope and Limitations. — The title reaction proceeds with high regio- and
29- 133 lidinones:
anti-selectivity but moderate diastereoselectivity. The nature of substituents plays an
important role on the outcome. Thus, alkenoyl, cinnamoyl, and electron-deficient cinnamoyl substrates bearing an isopropylated oxazolidinone ring smoothly undergo bromohydrin formation but no iodohydrination. In contrast, electron-rich cinnamoyl analogues are effectively transformed into carboxyiodohydrins, but their bromohydrination leads to mixtures of products. — (HAJRA*, S.; KARMAKAR, A.;
BHOWMICK, M.; Tetrahedron 61 (2005) 9, 2279-2286; Dep. Chem., Indian Inst.
Technol., Kharagpur 721 302, India; Eng.) — Jannicke
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