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2004
Cyclopentane derivatives
Q 0030
Inter- and Intramolecular [4 + 1]-Cycloadditions Between Electron-Poor Dienes
Electron-Rich Carbenes. — The [4+1]-cycloaddition of electron-poor dienes
49- 067 and
and electron-rich dialkoxycarbenes affording the corresponding cyclopentene adducts
is presented. The carbenes are generated through the thermal decomposition of oxadiazolines like (II). The prepared cyclopentene derivatives are obtained in moderate to
good yield and with high diastereoselectivity. The intramolecular version of this annulation reaction leads to bicyclic structures like (XI) and (XII). Additionally, a [4+1]-annulation with enone (XIII) giving the bicyclic ortho ester (XIV) is described. —
(SPINO*, C.; REZAEI, H.; DUPONT-GAUDET, K.; BELANGER, F.; J. Am. Chem.
Soc. 126 (2004) 32, 9926-9927; Dep. Chim., Fac. Sci., Univ. Sherbrooke, Sherbrooke,
Que. J1K 2R1, Can.; Eng.) — Bartels
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