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Stereoselective tandem Michael-intramolecular cyclization approach to functionalized pyrroloisoindolones

✍ Scribed by Adelfo Reyes; Ignacio Regla; Mabel C Fragoso; Laura A Vallejo; Patricia Demare; Hugo A Jiménez-Vázquez; Yara Ramírez; Eusebio Juaristi; Joaquín Tamariz

Book ID
104209584
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
787 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis

A stereoselective synthesis of pyrrolo[2,1-a]isoindoi-5-ones is described. The synthesis takes place through a tandem Michael addition-intramolecular cyclization, by the basepromoted 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 by a lithium chelate species between the interacting centers. The structure of the adducts is discussed, being supported by NMR experiments and X-ray crystallography.

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