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2001
cycloaddition reactions
cycloaddition reactions
O 0070
β,β’- and α,β,β’-Annulation Reactions of Cyclic Enamines: Enanof Bicyclo[3.n.1]alkenones (n = 2, 3) and
16 - 051 tioselective Synthesis
Tricyclo[3.3.0.02,8 ]octanes from Fischer Alkenyl Carbene Complexes.
— Chromium or tungsten alkenylcarbene like complexes (I) are very useful
C3-synthons for the [3 + 3] cycloaddition reaction toward cyclopentanone and
cyclohexanone enamines. Thus, the reaction of (I) and (II) in THF at 60◦ C
furnishes semibullvalenes (III) in high yields. Remarkable is the formation of
three carbon–carbon bonds and five stereogenic centers with total selectivity
in one step. Conducting the reaction of complexes (I) and enamines (II)
at lower temperatures, the compounds are transformed very efficiently into
functionalized bicyclooctanes (IV) and bicyclononanes (VII), resp., with high
diastereo- and enantioselectivity. — (BARLUENGA, JOSE; BALLESTEROS,
ALFREDO; SANTAMARIA, JAVIER; BERNARDO DE LA RUA, RAMON;
RUBIO, EDUARDO; TOMAS, MIGUEL; J. Am. Chem. Soc. 122 (2000)
51, 12874-12875; Inst. Quim. Organomet. ”Enrique Moles”, Univ. Oviedo,
E-33071 Oviedo, Spain; EN)
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