Functionalized organolithium compounds: Generation via reductive lithiation and nucleophilic addition to N-phenethylimides. Access to functionalized dihydropyrrolo[2,1-a]isoquinolinones
Izaskun Manteca
1
,
Begoña Etxarri
1
,
Ainhoa Ardeo
1
,
Sonia Arrasate
1
,
Iñaki Osante
1
,
Nuria Sotomayor
1
,
E. Lete
1
1
Departamento de Quı́mica Orgánica, Facultad de Ciencias, Universidad del Paı́s Vasco, Apdo. 644, 48080 Bilbao, Spain
|
Тип публикации: Journal Article
Дата публикации: 1998-10-01
scimago Q3
wos Q2
БС2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Краткое описание
A procedure for producing 1,4-dianion equivalents consists of reductive lithiation, induced by 4,4.-di- tert -butylbiphenylide, of functionalized phenyl sulfides. Nucleophilic addition of 4-lithio-2-(trimethylsilylmethyl)but-1-ene 1 and 2-(3-lithiopropyl)-2-trimethylsilyl-1,3-dithiane 2 thus prepared to N -phenethyl- cis -norbor-5-en-2,3-dicarboximide 9 afforded the corresponding α-hydroxy lactams in good yields. Besides, access to C-10b substituted α,β-unsaturated pyrroloisoquinolinones 3 was efficiently achieved via a tandem organolithium nucleophilic addition — N -acyliminium ion cyclization sequence and subsequent retro Diels-Alder reaction. The methodology can be extended to functionalized organolithiums, but the N -acyliminium cyclization fails if the allylsilane moiety is present. Graphic
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Manteca I. et al. Functionalized organolithium compounds: Generation via reductive lithiation and nucleophilic addition to N-phenethylimides. Access to functionalized dihydropyrrolo[2,1-a]isoquinolinones // Tetrahedron. 1998. Vol. 54. No. 40. pp. 12361-12378.
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Manteca I., Etxarri B., Ardeo A., Arrasate S., Osante I., Sotomayor N., Lete E. Functionalized organolithium compounds: Generation via reductive lithiation and nucleophilic addition to N-phenethylimides. Access to functionalized dihydropyrrolo[2,1-a]isoquinolinones // Tetrahedron. 1998. Vol. 54. No. 40. pp. 12361-12378.
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TY - JOUR
DO - 10.1016/S0040-4020(98)00745-5
UR - https://doi.org/10.1016/S0040-4020(98)00745-5
TI - Functionalized organolithium compounds: Generation via reductive lithiation and nucleophilic addition to N-phenethylimides. Access to functionalized dihydropyrrolo[2,1-a]isoquinolinones
T2 - Tetrahedron
AU - Manteca, Izaskun
AU - Etxarri, Begoña
AU - Ardeo, Ainhoa
AU - Arrasate, Sonia
AU - Osante, Iñaki
AU - Sotomayor, Nuria
AU - Lete, E.
PY - 1998
DA - 1998/10/01
PB - Elsevier
SP - 12361-12378
IS - 40
VL - 54
SN - 0040-4020
SN - 1464-5416
ER -
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@article{1998_Manteca,
author = {Izaskun Manteca and Begoña Etxarri and Ainhoa Ardeo and Sonia Arrasate and Iñaki Osante and Nuria Sotomayor and E. Lete},
title = {Functionalized organolithium compounds: Generation via reductive lithiation and nucleophilic addition to N-phenethylimides. Access to functionalized dihydropyrrolo[2,1-a]isoquinolinones},
journal = {Tetrahedron},
year = {1998},
volume = {54},
publisher = {Elsevier},
month = {oct},
url = {https://doi.org/10.1016/S0040-4020(98)00745-5},
number = {40},
pages = {12361--12378},
doi = {10.1016/S0040-4020(98)00745-5}
}
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MLA
Скопировать
Manteca, Izaskun, et al. “Functionalized organolithium compounds: Generation via reductive lithiation and nucleophilic addition to N-phenethylimides. Access to functionalized dihydropyrrolo[2,1-a]isoquinolinones.” Tetrahedron, vol. 54, no. 40, Oct. 1998, pp. 12361-12378. https://doi.org/10.1016/S0040-4020(98)00745-5.