Sulfone chemistry for the synthesis of C-branched pyrrolidines

The title compound, C14H19NO5S, was prepared by nucleophilic addition of the lithium derivative of methylphenylsulfone to (3S,4R)-3,4-isopropylidenedioxypyrroline 1-oxide. There are four molecules in the asymmetric unit. The crystal structure determination confirms the configuration of the chiral centres as 2R,3S,4R. In the crystal, pairs of O—H⋯N hydrogen bonds link the molecules into dimers.

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“…employed as starting material to tackle the synthesis of a C-branched substituted pyrrolidine (Flores et al, 2011a).…”

Section: Methodsmentioning

confidence: 99%

“…For the preparation, see: Flores et al (2010). For Cbranched pyrrolidines, see: Flores et al (2011a). For hydroxylamines in synthesis, see: Chevrier et al (2011); Li et al (2011).…”

Section: Related Literaturementioning

confidence: 99%

(2R,3S,4R)-3,4-Isopropylidenedioxy-2-(phenylsulfonylmethyl)pyrrolidin-1-ol

et al. 2012

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[3 + 2] Dipolar Cycloadditions of Cyclic Nitrones with Alkenes

et al. 2017

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The chapter describes the 1,3‐dipolar cycloadditions of cyclic nitrones with alkenes and surveys the literature from 1985 to 2014. In addition to comprehensive coverage of the cycloadditions reactions, which are presented in tables with experimental details, the introductory chapter describes methods for synthesizing cyclic nitrones, discusses mechanistic aspects of the cycloadditions and their scope, and furnishes selected examples of applications in the context of natural product synthesis.

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Synthesis of a Series of Enantiopure Polyhydroxylated Bicyclic N‐Heterocycles from an L‐Erythrose‐Derived Nitrone and Alkoxyallenes

2013

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Two different lithiated alkoxyallenes and the enantiopure L‐erythrose‐derived cyclic nitrone (+)‐3 were used as precursors for the preparation of novel bicyclic 2H‐1,2‐oxazine derivatives, which were formed as single diastereomers. A highly stereoselective hydroboration/oxidation sequence provided key substrates that were suitable for the synthesis of a series of polyhydroxylated bicyclic N‐heterocycles, including unique 5‐oxaindolizidines such as 8 and 12. Depending on the protecting groups installed, a straightforward ring‐opening/recyclization protocol allowed the preparation of the corresponding pyrrolizidines bearing two, three or four free hydroxy groups. By inversion of the order of reaction steps, the synthesis of novel isomeric azabicyclo[3.2.0]heptane derivatives that are the lower homologues of pyrrolizidines and indolizidines were achieved. The prepared novel polyhydroxylated compounds were examined for their property as glycosidase inhibitors, but none of the compounds showed noteworthy activity.

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Sulfone chemistry for the synthesis of C-branched pyrrolidines

Cited by 6 publications

References 41 publications

(2R,3S,4R)-3,4-Isopropylidenedioxy-2-(phenylsulfonylmethyl)pyrrolidin-1-ol

(2R,3S,4R)-3,4-Isopropylidenedioxy-2-(phenylsulfonylmethyl)pyrrolidin-1-ol

[3 + 2] Dipolar Cycloadditions of Cyclic Nitrones with Alkenes

Synthesis of a Series of Enantiopure Polyhydroxylated Bicyclic N‐Heterocycles from an L‐Erythrose‐Derived Nitrone and Alkoxyallenes

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