Studies on the Development of the Tritylsulfenyl Group as a Nitrogen Protecting Group and Application in a Synthesis of δ-Coniceine

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Abstract

The (triphenylmethyl)sulfenyl (tritylsulfenyl, TRS) group was found to possess properties which should make it useful as a nitrogen protecting group. The almost instantaneous reaction of TrSCl (6) with amines produced the corresponding triphenylmethanesulfenamides. The TRS group was found to render the nitrogen atom nonbasic and relatively nonnucleophilic, was stable to aqueous acid, aqueous base, and various reducing agents, and was moderately stable to Moffat oxidation conditions. The TRS group could be cleaved under mild conditions, generating the amine with either CuCl2/EtOH-THF, HI/THF-H20, or trimethylsilyl iodide (Me3SiI)/CH2Cl2. A synthesis of δ-coniceine (16) illustrates carbon-carbon bond formation with tritylsulfenimine methodology and the utility of the tritylsulfenyl group as a nitrogen protecting group.

Original languageEnglish (US)
Pages (from-to)3538-3544
Number of pages7
JournalJournal of Organic Chemistry
Volume48
Issue number20
DOIs
StatePublished - Jan 1 1983
Externally publishedYes

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Nitrogen
Amines
Carbon
Reducing Agents
Atoms
Oxidation
Acids
trimethylsilyl iodide
cupric chloride

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Studies on the Development of the Tritylsulfenyl Group as a Nitrogen Protecting Group and Application in a Synthesis of δ-Coniceine",
abstract = "The (triphenylmethyl)sulfenyl (tritylsulfenyl, TRS) group was found to possess properties which should make it useful as a nitrogen protecting group. The almost instantaneous reaction of TrSCl (6) with amines produced the corresponding triphenylmethanesulfenamides. The TRS group was found to render the nitrogen atom nonbasic and relatively nonnucleophilic, was stable to aqueous acid, aqueous base, and various reducing agents, and was moderately stable to Moffat oxidation conditions. The TRS group could be cleaved under mild conditions, generating the amine with either CuCl2/EtOH-THF, HI/THF-H20, or trimethylsilyl iodide (Me3SiI)/CH2Cl2. A synthesis of δ-coniceine (16) illustrates carbon-carbon bond formation with tritylsulfenimine methodology and the utility of the tritylsulfenyl group as a nitrogen protecting group.",
author = "Bruce Branchaud",
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publisher = "American Chemical Society",
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T1 - Studies on the Development of the Tritylsulfenyl Group as a Nitrogen Protecting Group and Application in a Synthesis of δ-Coniceine

AU - Branchaud, Bruce

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N2 - The (triphenylmethyl)sulfenyl (tritylsulfenyl, TRS) group was found to possess properties which should make it useful as a nitrogen protecting group. The almost instantaneous reaction of TrSCl (6) with amines produced the corresponding triphenylmethanesulfenamides. The TRS group was found to render the nitrogen atom nonbasic and relatively nonnucleophilic, was stable to aqueous acid, aqueous base, and various reducing agents, and was moderately stable to Moffat oxidation conditions. The TRS group could be cleaved under mild conditions, generating the amine with either CuCl2/EtOH-THF, HI/THF-H20, or trimethylsilyl iodide (Me3SiI)/CH2Cl2. A synthesis of δ-coniceine (16) illustrates carbon-carbon bond formation with tritylsulfenimine methodology and the utility of the tritylsulfenyl group as a nitrogen protecting group.

AB - The (triphenylmethyl)sulfenyl (tritylsulfenyl, TRS) group was found to possess properties which should make it useful as a nitrogen protecting group. The almost instantaneous reaction of TrSCl (6) with amines produced the corresponding triphenylmethanesulfenamides. The TRS group was found to render the nitrogen atom nonbasic and relatively nonnucleophilic, was stable to aqueous acid, aqueous base, and various reducing agents, and was moderately stable to Moffat oxidation conditions. The TRS group could be cleaved under mild conditions, generating the amine with either CuCl2/EtOH-THF, HI/THF-H20, or trimethylsilyl iodide (Me3SiI)/CH2Cl2. A synthesis of δ-coniceine (16) illustrates carbon-carbon bond formation with tritylsulfenimine methodology and the utility of the tritylsulfenyl group as a nitrogen protecting group.

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