Synthesis of a New Chiral Pyrrolidine

Flores, Mari Fe; Núñez, Marta G.; Moro, Rosalina F.; Garrido, Narciso M.; Marcos, Isidro S.; Iglesias, Enrique F; Garcı́a, Pilar Garcı́a; Dı́ez, David

doi:10.3390/molecules15031501

Cited by 6 publications

(4 citation statements)

References 36 publications

(35 reference statements)

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“…For proline and its derivatives as organocatalysts, see: Pellissier (2007); Lattanzi (2009); Mielgo et al (2008); Panday (2011). For the preparation, see: Flores et al (2010). For Cbranched pyrrolidines, see: Flores et al (2011a).…”

Section: Related Literaturementioning

confidence: 99%

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

et al. 2012

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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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Section: Related Literaturementioning

confidence: 99%

“…The title hydroxylamine, (II), was obtained stereoselectively by nucleophilic addition of lithio(phenylsulfonyl)methane to (3S,4R)-3,4-isopropylidenedioxypyrroline-1-oxide (I) according to the methodology described by us (Flores et al 2010).…”

Section: S2 Experimentalmentioning

confidence: 99%

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

et al. 2012

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“…For a related structure, see: Keleşog lu et al (2010). For the preparation of the title compound, see: Flores et al (2010); Cicchi et al (2006).…”

Section: Related Literaturementioning

confidence: 99%

“…The title N-oxide was obtained by intramolecular nucleophilic displacement, which is based on a simple one-pot procedure employing NH 2 OSiMe 2 t-Bu, methanesulfonyl chloride, and 2,3-O-iso-propylidene-D-erythronolactol, according to the methodology described by Cicchi et al (2006) and by us (Flores et al, 2010). Well shaped colourless single crystals were obtained by crystallization from CH 2 Cl 2 /MeOH.…”

Section: S2 Experimentalmentioning

confidence: 99%

(3R,4S)-3,4-Isopropylidenedioxy-3,4-dihydro-2H-pyrrole 1-oxide

Flores

Garcı́a

Garrido³

et al. 2011

Acta Cryst E

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The title compound C7H11NO3 was prepared by intramolecular nucleophilic displacement of 2,3-O-iso-propylidene-d-erythronolactol. There are two molecules in the asymmetric unit, which are related by a pseudo-inversion centre. The crystal structure determination confirms unequivocally the configuration of the chiral centres as 3S,4R. In the crystal structure, intermolecular C—H⋯O interactions link the molecules (into infinite zigzag chains along the a axis.

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