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200517.fm Page 117 Friday, March 18, 2005 2:52 PM
2005
Oxirane derivatives
R 0030
Effect of Tether Length on Ti(III)-Mediated Cyclization of Epoxyalkenes and
Epoxyketones. — The chemo- and regioselectivity of the title reactions
17- 108 Unsaturated
is studied. Epoxyalkenes (I) and (III) undergo only radical reduction to give dienols.
For epoxyalkenes (V) and (VIII), 5-exo- and 6-exo cyclizations are the main processes.
Epoxides (XI) and (XXV), bearing an exo carbonyl group with respect to the C=C double bond, preferentially undergo 3-exo and 5-endo cyclizations onto C=C, respectively.
For epoxides (XIII), (XV), (XIX) and (XXII), bearing an endo carbonyl group with
respect to the C=C double bond, 3-exo and 4-exo onto C=O, and 6-exo and 8-endo onto
C=C cyclization compounds are the major products, respectively. —
(FERNANDEZ-MATEO*, A.; MATEO BURON, L.; MARTIN DE LA NAVA, E. M.;
RABANEDO CLEMENTE, R.; RUBIO GONZALEZ, R.; SANZ GONZALEZ, F.;
Synlett 2004, 14, 2553-2557; Dep. Quim. Org., Fac. Cienc. Quim., Univ. Salamanca,
E-37008 Salamanca, Spain; Eng.) — Klein
200517.fm Page 118 Friday, March 18, 2005 2:52 PM
2005
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