Synthesis and crystal structure of (R, 4R)-3-[(N-benzyl-N-hydroxy-amino)-(1H-indol-3-yl)-methyl]-oxazolidin-2-one

David, Marion; Denis, Jean‐Noël; Philouze, Christian; Durif, A.; Vallée, Yannick

doi:10.1016/j.crci.2003.11.001

Cited by 4 publications

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References 17 publications

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“…When nitrone ( S )‐ 10 was added to indole under acidic conditions in methanol at 0 °C (Method A, Scheme ),13 a mixture of diastereoisomers 11a ( R ,4 S ) and 11b ( S ,4 S )13c in a 3:2 ratio (determined by 1 H NMR of crude mixture) was obtained. Compounds 11a and 11b were isolated in 32 % and 20 % yield, respectively.…”

Section: Resultsmentioning

confidence: 99%

Heterolignans: Stereoselective Synthesis of an 11‐Amino Analog of Azaelliptitoxin

et al. 2008

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The 11‐amino‐azaelliptitoxin analog (11R,11aS,5R)‐15 has been prepared stereoselectively in eight steps and 24 % overall yield from commercially available (S)‐glycidol (7) via the original enantiopure chiral α‐amino aldehyde 9, used as chiral precursor for the creation of the two other stereogenic centers of the target framework. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Section: Resultsmentioning

confidence: 99%

Heterolignans: Stereoselective Synthesis of an 11‐Amino Analog of Azaelliptitoxin

et al. 2008

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The (3+2)- and formal (3+3)-cycloadditions of N-vinylpyrroles with cyclic nitrones and C,N-cyclic azomethine imines

et al. 2018

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Efficient stereoselective nucleophilic addition of pyrroles to chiral nitrones

et al. 2008

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Regioselective additions of pyrroles to a variety of optically active nitrones under smooth acidic conditions lead to chiral pyrrolic N-hydroxylamines in good to excellent yields. Depending on the position of the chirality on the nitrone partner, the addition products have been isolated with high diastereoselectivity levels. Reaction of glyoxylate based chiral nitrones either at the C-2 or at the C-3 position of the pyrrole nucleus afforded N-hydroxyamino esters in high yields as single diastereoisomers. These adducts allow access to enantio-enriched non proteinogenic 2'- and 3'-pyrrolylglycines (13 and 19 respectively).

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Synthesis and crystal structure of (R, 4R)-3-[(N-benzyl-N-hydroxy-amino)-(1H-indol-3-yl)-methyl]-oxazolidin-2-one

Cited by 4 publications

References 17 publications

Heterolignans: Stereoselective Synthesis of an 11‐Amino Analog of Azaelliptitoxin

Heterolignans: Stereoselective Synthesis of an 11‐Amino Analog of Azaelliptitoxin

The (3+2)- and formal (3+3)-cycloadditions of N-vinylpyrroles with cyclic nitrones and C,N-cyclic azomethine imines

Efficient stereoselective nucleophilic addition of pyrroles to chiral nitrones

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