Stereoselective tandem Michael-intramolecular cyclization approach to functionalized pyrroloisoindolones

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

doi:10.1016/S0040-4020(99)00645-6

Stereoselective tandem Michael-intramolecular cyclization approach to functionalized pyrroloisoindolones

Adelfo Reyes, Ignacio Regla, Mabel C. Fragoso, Laura A. Vallejo, Patricia Demare, Hugo A. Jiménez-Vázquez, Yara Ramírez, Eusebio Juaristi, Joaquín Tamariz

Escuela Nacional de Ciencias Biológicas (ENCB)

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

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 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.

Original language	English
Pages (from-to)	11187-11202
Number of pages	16
Journal	Tetrahedron
Volume	55
Issue number	37
DOIs	https://doi.org/10.1016/S0040-4020(99)00645-6
State	Published - 10 Sep 1999

Keywords

Cyclization
Michael reactions
N-phthaloylalaninate
Pyrroloisoindolones

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10.1016/S0040-4020(99)00645-6

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title = "Stereoselective tandem Michael-intramolecular cyclization approach to functionalized pyrroloisoindolones",

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 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.",

keywords = "Cyclization, Michael reactions, N-phthaloylalaninate, Pyrroloisoindolones",

author = "Adelfo Reyes and Ignacio Regla and Fragoso, {Mabel C.} and Vallejo, {Laura A.} and Patricia Demare and Jim{\'e}nez-V{\'a}zquez, {Hugo A.} and Yara Ram{\'i}rez and Eusebio Juaristi and Joaqu{\'i}n Tamariz",

year = "1999",

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doi = "10.1016/S0040-4020(99)00645-6",

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volume = "55",

pages = "11187--11202",

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TY - JOUR

T1 - Stereoselective tandem Michael-intramolecular cyclization approach to functionalized pyrroloisoindolones

AU - Reyes, Adelfo

AU - Regla, Ignacio

AU - Fragoso, Mabel C.

AU - Vallejo, Laura A.

AU - Demare, Patricia

AU - Jiménez-Vázquez, Hugo A.

AU - Ramírez, Yara

AU - Juaristi, Eusebio

AU - Tamariz, Joaquín

PY - 1999/9/10

Y1 - 1999/9/10

N2 - 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 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.

AB - 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 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.

KW - Cyclization

KW - Michael reactions

KW - N-phthaloylalaninate

KW - Pyrroloisoindolones

UR - http://www.scopus.com/inward/record.url?scp=0033543472&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(99)00645-6

DO - 10.1016/S0040-4020(99)00645-6

M3 - Artículo

SN - 0040-4020

VL - 55

SP - 11187

EP - 11202

JO - Tetrahedron

JF - Tetrahedron

IS - 37

ER -

Stereoselective tandem Michael-intramolecular cyclization approach to functionalized pyrroloisoindolones

Abstract

Keywords

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