Diastereoselective hetero-diels-alder cycloaddition of a C-nitroso compound prepared starting from a homochiral imidazolidin-2-one

Barbara Cardillo; Roberta Galeazzi; Giovanna Mobbili; Mario Orena; Monica Rossetti

doi:10.1016/0957-4166(94)80123-1

Diastereoselective hetero-diels-alder cycloaddition of a C-nitroso compound prepared starting from a homochiral imidazolidin-2-one

Barbara Cardillo, Roberta Galeazzi, Giovanna Mobbili, Mario Orena, Monica Rossetti

Istituto Nazionale di Riposo e Cura per Anziani V.E. II

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

Abstract

By Swern oxidation of the hydroxamic acid 3, prepared from the homochiral imidazolidin-2-one 1, the transient C-nitroso derivative 4 is obtained, and its cycloaddition to either cyclohexadiene or cyclopentadiene proceeds with high diastereoselection, owing to the conformational stability of 4. The stereochemical outcome of the reaction is determined from ¹H NMR data and further confirmed by the specific rotation value of 7, obtained by cleavage of the major cycloadduct 5a.

Original language	English
Pages (from-to)	1535-1540
Number of pages	6
Journal	Tetrahedron: Asymmetry
Volume	5
Issue number	8
DOIs	https://doi.org/10.1016/0957-4166(94)80123-1
Publication status	Published - 1994

ASJC Scopus subject areas

Inorganic Chemistry
Organic Chemistry
Materials Chemistry
Drug Discovery

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title = "Diastereoselective hetero-diels-alder cycloaddition of a C-nitroso compound prepared starting from a homochiral imidazolidin-2-one",

abstract = "By Swern oxidation of the hydroxamic acid 3, prepared from the homochiral imidazolidin-2-one 1, the transient C-nitroso derivative 4 is obtained, and its cycloaddition to either cyclohexadiene or cyclopentadiene proceeds with high diastereoselection, owing to the conformational stability of 4. The stereochemical outcome of the reaction is determined from 1H NMR data and further confirmed by the specific rotation value of 7, obtained by cleavage of the major cycloadduct 5a.",

author = "Barbara Cardillo and Roberta Galeazzi and Giovanna Mobbili and Mario Orena and Monica Rossetti",

year = "1994",

doi = "10.1016/0957-4166(94)80123-1",

language = "English",

volume = "5",

pages = "1535--1540",

journal = "Tetrahedron Asymmetry",

issn = "0957-4166",

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T1 - Diastereoselective hetero-diels-alder cycloaddition of a C-nitroso compound prepared starting from a homochiral imidazolidin-2-one

AU - Cardillo, Barbara

AU - Galeazzi, Roberta

AU - Mobbili, Giovanna

AU - Orena, Mario

AU - Rossetti, Monica

PY - 1994

Y1 - 1994

N2 - By Swern oxidation of the hydroxamic acid 3, prepared from the homochiral imidazolidin-2-one 1, the transient C-nitroso derivative 4 is obtained, and its cycloaddition to either cyclohexadiene or cyclopentadiene proceeds with high diastereoselection, owing to the conformational stability of 4. The stereochemical outcome of the reaction is determined from 1H NMR data and further confirmed by the specific rotation value of 7, obtained by cleavage of the major cycloadduct 5a.

AB - By Swern oxidation of the hydroxamic acid 3, prepared from the homochiral imidazolidin-2-one 1, the transient C-nitroso derivative 4 is obtained, and its cycloaddition to either cyclohexadiene or cyclopentadiene proceeds with high diastereoselection, owing to the conformational stability of 4. The stereochemical outcome of the reaction is determined from 1H NMR data and further confirmed by the specific rotation value of 7, obtained by cleavage of the major cycloadduct 5a.

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JF - Tetrahedron Asymmetry

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