Synthesis of functionalized non‐natural amino acid derivatives via amidoalkylation transformations

P, LeGall; Sawhney, K. N.; Conley, Judith D.; Kohn, Harold

doi:10.1111/j.1399-3011.1988.tb01262.x

Cited by 5 publications

(1 citation statement)

References 6 publications

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“…To the best of our knowledge, only one derivative of compound 13 has been previously synthesized in racemic form and moderate yield. 26 Hydroxylamine 11 was subsequently converted into 10a in acidic methanol (89%). Upon treatment with H 2 (1 atm) in the presence of black palladium in a MeOH-HCOOH mixture (9 : 1), concomitant reduction of the N-hydroxylamine moiety and deprotection of the benzyl group were observed in 40% yield.…”

Section: Resultsmentioning

confidence: 99%

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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Section: Resultsmentioning

confidence: 99%

Efficient stereoselective nucleophilic addition of pyrroles to chiral nitrones

et al. 2008

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ChemInform Abstract: Synthesis of Functionalized Non‐Natural Amino Acid Derivatives via Amidoalkylation Transformations.

Sawhney

Conley

et al. 1989

ChemInform

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ChemInform Abstract Two different synthetic approaches to amino acid amides bearing a (hetero)aryl substituent in the α-position are examined. Treatment of the 2-acetamido-2-methoxyacetate (I) with furan (II) or pyrrole (IV) in the presence of boron trifluoride etherate gives the functionalized α-amino esters (III) or (V) and (VI). (III) is converted to the benzylamide (VIIIc) by conventional methods. Better results are achieved when the acetamidoethoxyacetate (IX) is first transformed into the benzamide (X) and the (het)aryl substitutent is introduced in the second step, producing (VIII).

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