Contrasting Carboannulation Involving δ-Acetoxy Allenoate as a Four-Carbon Synthon Using DABCO and DMAP: Access to Spiro-carbocyclic and m-Teraryl Scaffolds
Spiro-annulation involving delta-acetoxy allenoate and alkyl benzoisothiazole dioxide (N-sulfonyl ketimine) triggered by DABCO/MeCO2H combination leads to an essentially single diastereomer via chemo- and regiospecific [4 + 2]-carboannulation and a new hydroxyl group is introduced. In contrast, DMAP...
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| Vydáno v: | Organic letters Ročník 23; číslo 3; s. 1123 - 1129 |
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| Médium: | Journal Article |
| Jazyk: | angličtina |
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WASHINGTON
Amer Chemical Soc
05.02.2021
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| ISSN: | 1523-7060, 1523-7052, 1523-7052 |
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| Abstract | Spiro-annulation involving delta-acetoxy allenoate and alkyl benzoisothiazole dioxide (N-sulfonyl ketimine) triggered by DABCO/MeCO2H combination leads to an essentially single diastereomer via chemo- and regiospecific [4 + 2]-carboannulation and a new hydroxyl group is introduced. In contrast, DMAP-catalyzed benzannulation using the same reactants affords unsymmetrical m-teraryls via Mannich coupling, sequential proton transfers, and C-N bond cleavage. Here, delta-acetoxy allenoate serves as a 4C-synthon and the carboannulation is completely base dependent and mutually exclusive. |
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| AbstractList | Spiro-annulation involving delta-acetoxy allenoate and alkyl benzoisothiazole dioxide (N-sulfonyl ketimine) triggered by DABCO/MeCO2H combination leads to an essentially single diastereomer via chemo- and regiospecific [4 + 2]-carboannulation and a new hydroxyl group is introduced. In contrast, DMAP-catalyzed benzannulation using the same reactants affords unsymmetrical m-teraryls via Mannich coupling, sequential proton transfers, and C-N bond cleavage. Here, delta-acetoxy allenoate serves as a 4C-synthon and the carboannulation is completely base dependent and mutually exclusive. Spiro-annulation involving δ-acetoxy allenoate and alkyl benzoisothiazole dioxide (N-sulfonyl ketimine) triggered by DABCO/MeCO2H combination leads to an essentially single diastereomer via chemo- and regiospecific [4 + 2]-carboannulation and a new hydroxyl group is introduced. In contrast, DMAP-catalyzed benzannulation using the same reactants affords unsymmetrical m-teraryls via Mannich coupling, sequential proton transfers, and C-N bond cleavage. Here, δ-acetoxy allenoate serves as a 4C-synthon and the carboannulation is completely base dependent and mutually exclusive.Spiro-annulation involving δ-acetoxy allenoate and alkyl benzoisothiazole dioxide (N-sulfonyl ketimine) triggered by DABCO/MeCO2H combination leads to an essentially single diastereomer via chemo- and regiospecific [4 + 2]-carboannulation and a new hydroxyl group is introduced. In contrast, DMAP-catalyzed benzannulation using the same reactants affords unsymmetrical m-teraryls via Mannich coupling, sequential proton transfers, and C-N bond cleavage. Here, δ-acetoxy allenoate serves as a 4C-synthon and the carboannulation is completely base dependent and mutually exclusive. Spiro-annulation involving δ-acetoxy allenoate and alkyl benzoisothiazole dioxide ( -sulfonyl ketimine) triggered by DABCO/MeCO H combination leads to an via chemo- and regiospecific [4 + 2]-carboannulation and a new group is introduced. In contrast, DMAP-catalyzed benzannulation using the same reactants affords unsymmetrical -teraryls via Mannich coupling, sequential proton transfers, and C-N bond cleavage. Here, δ-acetoxy allenoate serves as a 4C-synthon and the carboannulation is completely base dependent and mutually exclusive. |
| Author | Swamy, K. C. Kumara Kumar, A. Sanjeeva Chauhan, Sachin |
| Author_xml | – sequence: 1 givenname: A. Sanjeeva surname: Kumar fullname: Kumar, A. Sanjeeva organization: Univ Hyderabad, Sch Chem, Hyderabad 500046, Telangana, India – sequence: 2 givenname: Sachin surname: Chauhan fullname: Chauhan, Sachin organization: Univ Hyderabad, Sch Chem, Hyderabad 500046, Telangana, India – sequence: 3 givenname: K. C. Kumara orcidid: 0000-0002-7617-706X surname: Swamy fullname: Swamy, K. C. Kumara email: kckssc@uohyd.ac.in organization: Univ Hyderabad, Sch Chem, Hyderabad 500046, Telangana, India |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/33480700$$D View this record in MEDLINE/PubMed |
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| Snippet | Spiro-annulation involving delta-acetoxy allenoate and alkyl benzoisothiazole dioxide (N-sulfonyl ketimine) triggered by DABCO/MeCO2H combination leads to an... Spiro-annulation involving δ-acetoxy allenoate and alkyl benzoisothiazole dioxide ( -sulfonyl ketimine) triggered by DABCO/MeCO H combination leads to an via... Spiro-annulation involving δ-acetoxy allenoate and alkyl benzoisothiazole dioxide (N-sulfonyl ketimine) triggered by DABCO/MeCO2H combination leads to an... |
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| Title | Contrasting Carboannulation Involving δ-Acetoxy Allenoate as a Four-Carbon Synthon Using DABCO and DMAP: Access to Spiro-carbocyclic and m-Teraryl Scaffolds |
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