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Synthesis of 5-substituted pipecolic acid derivatives as new conformationally constrained ornithine and arginine analogues

Autor: Laurent Le Corre, H. Dhimane

Publikováno v: Tetrahedron Letters. 46:7495-7497

Two, orthogonally protected, constrained analogues of arginine have been synthesised in a diastereodivergent manner. The key step involved an electrophilic or radical functionalisation of methyl N-Boc-5,6-dehydropipecolate.

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::d9e62de073d9bfce81c43d011ff3260f
https://doi.org/10.1016/j.tetlet.2005.09.008

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ChemInform Abstract: Tandem Zinc Mediated Reductive Cleavage-Reductive Amination as a New Approach to Substituted Pyrrolidines from Homoallylic Amines

Autor: H. Dhimane, Valérie Verdel, Gérard Lhommet, Xavier Brusson, C. Vanucci, Frédérique Zana

Publikováno v: ChemInform. 26

N-Boc or N-Cbz homoallylic amines are converted in four steps into pyrrolidines through a sequence involving as a key-step a tandem zinc mediated reductive cleavage-reductive amination from an intermediate 1,3-oxazin-2-one

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::52fa79977fcd61a7c8288c60958b2c88
https://doi.org/10.1002/chin.199534143

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ChemInform Abstract: Unexpected Diastereoselectivity in the Formation of 3,5-Disubstituted Indolizidines by Intramolecular Reductive Amination

Autor: C. Celimene, G. Lhommet, A. Saboureau, H. Dhimane

Publikováno v: ChemInform. 27

The reductive amination of appropriate ketopyrrolidines leading to 3,5-dialkylindolizidines usually gives stereoselectively the indolizidine with a cis relative stereochemistry on the piperidine moiety. We report herein unexpected results concerning

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::b9497b6d5ed91c4c46c6616ca9833eb2
https://doi.org/10.1002/chin.199640198

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ChemInform Abstract: Stereoselective Access to trans-2,5-Disubstituted Pyrrolidine Derivatives by Nucleophilic Addition to Bicyclic N-Acyliminium Ion

Autor: C. Vanucci, H. Dhimane, Gérard Lhommet

Publikováno v: ChemInform. 28

5-Alkoxy-pyrroloxazolidin-3-ones 1 were stereoselectively prepared from (S)-pyroglutamic acid. Treatment of 1 with a Lewis acid generated in situ the N-acyliminium 2 , which was trapped by various π-nucleophiles leading selectively to trans pyrrolid

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::76565628dc082abbaae13249e3cb6f87
https://doi.org/10.1002/chin.199724132

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ChemInform Abstract: Synthesis of New Trialkylsilylmethyloxazinones via Intramolecular Trapping of β-Silyl Carbocations by an N-Boc Group

Autor: H. Dhimane, Gérard Lhommet, Jean-Christophe Poupon, Sylvie Brocherieux-Lanoy, C. Vanucci

Publikováno v: ChemInform. 28

N -Boc amino ethers 1a–e when treated with allyltrialkylsilanes in the presence of TiCl4 afford the expected allylation compounds 2a–e and/or the unprecedented silylated oxazinones 3a–e or 4a–e.

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::e7571d4a38cb13abf5ffcf05fe56d5b3
https://doi.org/10.1002/chin.199749175

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