Tetrahedron

Stereoselective tandem Michael-intramolecular cyclization approach to functionalized pyrroloisoindolones

…, P Demare, HA Jiménez-Vázquez, Y Ramírez…

Index: Reyes, Adelfo; Regla, Ignacio; Fragoso, Mabel C.; Vallejo, Laura A.; Demare, Patricia; Jimenez-Vazquez, Hugo A.; Ramirez, Yara; Juaristi, Eusebio; Tamariz, Joaquin Tetrahedron, 1999 , vol. 55, # 37 p. 11187 - 11202

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Citation Number: 9

Abstract

A stereoselective synthesis of pyrrolo [2, 1-a] isoindol-5-ones is described. The synthesis takes place through a tandem Michael addition-intramolecular cyclization, by the base- promoted condensation of methyl N-phthaloylalaninate with conjugate acceptors at low temperature. The desired products were obtained in good yields as single isomers in only one step. Presumably, the stereoselectivity of the cyclization step is kinetically controlled ...