Regio- and diastereo-selectivity in 1,3-dipolar cycloadditions of nitrile oxides to 4-substituted cyclopent-2-enones

Adembri, G.; Giorgi, Gianluca; Lampariello, Raffaella; Paoli, M. Laura; Sega, Alessandro

doi:10.1039/b003549l

Cited by 21 publications

(12 citation statements)

References 36 publications

(29 reference statements)

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“…This methodology proved to be very general and may be extended to other α,β-unsaturated cyclic ketones and to different nitrile oxides. [12] Experimental Section General: Melting points were determined using a Kofler apparatus and are uncorrected. Elemental analysis was performed with a PerkinϪElmer 240C elemental analyser.…”

Section: Resultsmentioning

confidence: 99%

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Developing Molecular Diversity in the Construction of a Family of Bicyclic Isoxazolines Scaffolds: Control of Regio‐and Diastereoselectivities

Giorgi¹,

Lampariello²,

Minetto³

et al. 2003

Eur J Org Chem

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A completely regioselective approach to bicyclic isoxazolines has been found starting from 4‐cyclopentene‐1,3‐dione or 2‐cyclopentenones. 1,3‐Dipolar cycloaddition with nitrile oxides gave different semirigid bicyclic scaffolds with at least four points of elaboration for molecular diversity. From these intermediates, two families of regioisomer isoxazolines can be prepared with complete control of their relative stereochemistry. Further elaboration of functional groups was demonstrated in order to exploit a successive parallel preparation of arrays of compounds. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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Section: Resultsmentioning

confidence: 99%

“…[12] The facial diastereoselectivity of the reaction depended on the nature of the groups at the allylic positions and, in some cases, on the nature of the solvent. [13] On the other hand, the regioselectivity of the reactions was independent of the nature of the substituents, nitrile oxides, and solvent employed.…”

Section: Introductionmentioning

confidence: 99%

Developing Molecular Diversity in the Construction of a Family of Bicyclic Isoxazolines Scaffolds: Control of Regio‐and Diastereoselectivities

Giorgi¹,

Lampariello²,

Minetto³

et al. 2003

Eur J Org Chem

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“…Independently, the research groups of Mann [88] and Sega [89] examined [3+2] cycloaddition reactions between nitriloxide and the enone moiety of 4-hydroxy-2-cyclopentenone derivatives (Scheme 46). Mann et al reported the highly diastereoselective cycloaddition of a range of nitriloxides with the 4-silyloxy-2-cyclopentenone (S)-122, giving anti isoxazoline products 246.…”

Section: 5c [3+2] Cycloadditionsmentioning

confidence: 99%

Chemistry of 4‐Hydroxy‐2‐cyclopentenone Derivatives

Roche

Aitken

2010

Eur J Org Chem

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“…Diol 14 was prepared in racemic form from 2,5-dimethylfuran (15) via 16 and the known ketone 17 [9] (Scheme 3). It should be noted that prolonged reaction times for the production of 17 lead to formation of the thermodynamically more-stable constitutional isomer 18, conceivably via 19a,b as shown in Scheme 3.…”

Section: Scheme 2 Retrosynthetic Analysis Ofmentioning

confidence: 99%

Toward a Total Synthesis of Macrocyclic Jatrophane Diterpenes – Concise Route to a Highly Functionalized Cyclopentane Key Intermediate

Mulzer¹,

Giester²,

Gilbert³

2005

Helvetica Chimica Acta

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Dedicated to Professor Rolf Huisgen on the occasion of his 85th birthday A total synthesis of the biologically potent jatrophane diterpenes pepluanin A (1) and euphosalicin A (2) is being aimed at. En route to these targets, a concise synthesis of the nonracemic cyclopentane building block 74 was developed. Key steps were a Claisen ± Eschenmoser rearrangement of the enantiomerically enriched allylic alcohol 14 to amide 34 (Scheme 7), a hydroxy-lactonization of 40 to 43 (Scheme 9), followed by translactonization to 72, which was subjected to a Davis hydroxylation to 69 (Scheme 17). Eventually, compound 69 was converted into the enol triflate 74. This material should prove suitable for an annulation of the macrocyclic ring characteristic of the desired jatrophanes 1 and 2. Less-successful approaches are also discussed due to their intrinsically valuable information content.

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Regio- and diastereo-selectivity in 1,3-dipolar cycloadditions of nitrile oxides to 4-substituted cyclopent-2-enones

Cited by 21 publications

References 36 publications

Developing Molecular Diversity in the Construction of a Family of Bicyclic Isoxazolines Scaffolds: Control of Regio‐and Diastereoselectivities

Developing Molecular Diversity in the Construction of a Family of Bicyclic Isoxazolines Scaffolds: Control of Regio‐and Diastereoselectivities

Chemistry of 4‐Hydroxy‐2‐cyclopentenone Derivatives

Toward a Total Synthesis of Macrocyclic Jatrophane Diterpenes – Concise Route to a Highly Functionalized Cyclopentane Key Intermediate

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