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2005
Oxirane derivatives
R 0030
Isomerization of (E)-α,β-Epoxyamides to (Z)-α,β-Epoxyamides and Synthetic
Based on Regio- and Stereoselective Oxirane Ring Openings. — An
11- 118 Applications
efficient isomerization of the trans epoxide (I) to its cis isomer (IV) is achieved via
highly stereoselective epoxide ring opening with LiI. The reaction of (IV) with various
nucleophiles affords syn products required in carbohydrate chemistry. Additionally, a
number of less successful routes for the targeted epoxide (IV) are described in detail.
— (MARTIN-ORTIZ, L.; CHAMMAA, S.; PINO-GONZALEZ, M. S.;
SANCHEZ-RUIZ, A.; GARCIA-CASTRO, M.; ASSIEGO, C.; SARABIA*, F.;
Tetrahedron Lett. 45 (2004) 49, 9069-9072; Dep. Bioquim., Biol. Mol. Quim. Org.,
Fac. Cienc., Univ. Malaga, E-29071 Malaga, Spain; Eng.) — Mais
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