Divergent Reactivity of δ- and β'-Acetoxy Allenoates with 2-Sulfonamidoindoles via Phosphine Catalysis: Entry to Dihydro-α-carboline, α-Carboline, and Spiro-cyclopentene Motifs
The reactivity of 2-sulfonamidoindoles with acetoxy allenoates under phosphine catalysis depends on the disposition of the acetoxy (OAc) group on the allenoate. In the temperature-controlled [3 + 3] annulations, d-acetoxy allenoates afforded dihydrocarboline and carboline scaffolds with carbon-nitro...
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| Veröffentlicht in: | Journal of organic chemistry Jg. 86; H. 17; S. 11583 - 11598 |
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| Sprache: | Englisch |
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Amer Chemical Soc
03.09.2021
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| ISSN: | 0022-3263, 1520-6904, 1520-6904 |
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| Abstract | The reactivity of 2-sulfonamidoindoles with acetoxy allenoates under phosphine catalysis depends on the disposition of the acetoxy (OAc) group on the allenoate. In the temperature-controlled [3 + 3] annulations, d-acetoxy allenoates afforded dihydrocarboline and carboline scaffolds with carbon-nitrogen nucleophilic 2-sulfonamidoindoles, in which allenoate serves as a beta-, gamma-, and delta-carbon donor. At room temperature (25 degrees C), dihydro-alpha-carboline motifs were obtained exclusively through Michael addition, 1,4-proton shift, isomerization, 1,2-proton transfer, phosphine elimination, and aza-Michael addition. The higher temperature (80 degrees C) cascade protocol using Ph3P-Cs2CO3 combination involves addition-elimination, aza-Claisen rearrangement, tosyl migration, and aromatization as key steps to give alpha-carbolines containing tosyl functionality at the gamma-carbon. In contrast, with beta'-acetoxy allenoate, 2-sulfonamidoindole acts only as a carbo-nucleophile in (p-tolyl)(3)P-directed [4 + 1] spiro-annulation, leading to five-membered spiro-carbocyclic motifs essentially as single diastereomers (dr >20:1) via chemoselective carbo-annulation. |
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| AbstractList | The reactivity of 2-sulfonamidoindoles with acetoxy allenoates under phosphine catalysis depends on the disposition of the acetoxy (OAc) group on the allenoate. In the temperature-controlled [3 + 3] annulations, δ-acetoxy allenoates afforded dihydrocarboline and carboline scaffolds with carbon-nitrogen nucleophilic 2-sulfonamidoindoles, in which allenoate serves as a β-, γ-, and δ-carbon donor. At room temperature (25 °C), dihydro-α-carboline motifs were obtained exclusively through Michael addition, 1,4-proton shift, isomerization, 1,2-proton transfer, phosphine elimination, and aza-Michael addition. The higher temperature (80 °C) cascade protocol using Ph3P-Cs2CO3 combination involves addition-elimination, aza-Claisen rearrangement, tosyl migration, and aromatization as key steps to give α-carbolines containing tosyl functionality at the γ-carbon. In contrast, with β'-acetoxy allenoate, 2-sulfonamidoindole acts only as a carbo-nucleophile in (p-tolyl)3P-directed [4 + 1] spiro-annulation, leading to five-membered spiro-carbocyclic motifs essentially as single diastereomers (dr >20:1) via chemoselective carbo-annulation.The reactivity of 2-sulfonamidoindoles with acetoxy allenoates under phosphine catalysis depends on the disposition of the acetoxy (OAc) group on the allenoate. In the temperature-controlled [3 + 3] annulations, δ-acetoxy allenoates afforded dihydrocarboline and carboline scaffolds with carbon-nitrogen nucleophilic 2-sulfonamidoindoles, in which allenoate serves as a β-, γ-, and δ-carbon donor. At room temperature (25 °C), dihydro-α-carboline motifs were obtained exclusively through Michael addition, 1,4-proton shift, isomerization, 1,2-proton transfer, phosphine elimination, and aza-Michael addition. The higher temperature (80 °C) cascade protocol using Ph3P-Cs2CO3 combination involves addition-elimination, aza-Claisen rearrangement, tosyl migration, and aromatization as key steps to give α-carbolines containing tosyl functionality at the γ-carbon. In contrast, with β'-acetoxy allenoate, 2-sulfonamidoindole acts only as a carbo-nucleophile in (p-tolyl)3P-directed [4 + 1] spiro-annulation, leading to five-membered spiro-carbocyclic motifs essentially as single diastereomers (dr >20:1) via chemoselective carbo-annulation. The reactivity of 2-sulfonamidoindoles with acetoxy allenoates under phosphine catalysis depends on the disposition of the acetoxy (OAc) group on the allenoate. In the temperature-controlled [3 + 3] annulations, d-acetoxy allenoates afforded dihydrocarboline and carboline scaffolds with carbon-nitrogen nucleophilic 2-sulfonamidoindoles, in which allenoate serves as a beta-, gamma-, and delta-carbon donor. At room temperature (25 degrees C), dihydro-alpha-carboline motifs were obtained exclusively through Michael addition, 1,4-proton shift, isomerization, 1,2-proton transfer, phosphine elimination, and aza-Michael addition. The higher temperature (80 degrees C) cascade protocol using Ph3P-Cs2CO3 combination involves addition-elimination, aza-Claisen rearrangement, tosyl migration, and aromatization as key steps to give alpha-carbolines containing tosyl functionality at the gamma-carbon. In contrast, with beta'-acetoxy allenoate, 2-sulfonamidoindole acts only as a carbo-nucleophile in (p-tolyl)(3)P-directed [4 + 1] spiro-annulation, leading to five-membered spiro-carbocyclic motifs essentially as single diastereomers (dr >20:1) via chemoselective carbo-annulation. |
| Author | Swamy, K. C. Kumara Debnath, Shubham Chauhan, Sachin Kumar, A. Sanjeeva |
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| Keywords | MIGRATION CYCLOADDITION REACTIONS ADDITION/CYCLOADDITION ENANTIOSELECTIVE SYNTHESIS ASYMMETRIC 3+2 ANNULATIONS BENZOFURANS ALLENES CYCLIZATION ACCESS INDOLES |
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| Snippet | The reactivity of 2-sulfonamidoindoles with acetoxy allenoates under phosphine catalysis depends on the disposition of the acetoxy (OAc) group on the... |
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| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | Divergent Reactivity of δ- and β'-Acetoxy Allenoates with 2-Sulfonamidoindoles via Phosphine Catalysis: Entry to Dihydro-α-carboline, α-Carboline, and Spiro-cyclopentene Motifs |
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