Organocatalytic Diastereoselective Synthesis of Diazoaryl-benzo[b]azepine Derivatives

Koppanathi Nagaraju; Ramani Gurubrahamam; Ramani Gurubrahamam; Kwunmin Chen

doi:10.1021/acs.joc.0c00431

Organocatalytic Diastereoselective Synthesis of Diazoaryl-benzo[b]azepine Derivatives

Koppanathi Nagaraju, Ramani Gurubrahamam, Ramani Gurubrahamam, Kwunmin Chen^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

15 引文斯高帕斯（Scopus）

摘要

To construct multisubstituted seven-membered nitrogenous heterocyclic scaffolds, an efficient method, employing 2-aminoaryl N-monosubstituted hydrazones and 2-oxo-3-butenoates under Brønsted acid catalysis, has been developed. This strategy highlights the umpolung reactivity of 2-aminobenzaldehyde arylhydrazones toward 2-oxo-3-butenoates to afford (E)-diazoaryl-benzo[b]azepine derivatives in excellent yields (89-99%) and with high diastereoselectivities (>19:1 dr).

原文	英語
頁（從 - 到）	7060-7067
頁數	8
期刊	Journal of Organic Chemistry
卷	85
發行號	11
DOIs	https://doi.org/10.1021/acs.joc.0c00431
出版狀態	已發佈 - 2020 6月 5

ASJC Scopus subject areas

有機化學

存取文件

10.1021/acs.joc.0c00431

其它文件與鏈接

CCDC 1940881: Experimental Crystal Structure Determination
Nagaraju, K. (Contributor), Gurubrahamam, R. (Contributor) & Chen, K. (Contributor), Unknown Publisher, 2020
DOI: 10.5517/ccdc.csd.cc234n20, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc234n20&sid=DataCite
資料集: Dataset

引用此

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abstract = "To construct multisubstituted seven-membered nitrogenous heterocyclic scaffolds, an efficient method, employing 2-aminoaryl N-monosubstituted hydrazones and 2-oxo-3-butenoates under Br{\o}nsted acid catalysis, has been developed. This strategy highlights the umpolung reactivity of 2-aminobenzaldehyde arylhydrazones toward 2-oxo-3-butenoates to afford (E)-diazoaryl-benzo[b]azepine derivatives in excellent yields (89-99%) and with high diastereoselectivities (>19:1 dr).",

author = "Koppanathi Nagaraju and Ramani Gurubrahamam and Ramani Gurubrahamam and Kwunmin Chen",

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PY - 2020/6/5

Y1 - 2020/6/5

N2 - To construct multisubstituted seven-membered nitrogenous heterocyclic scaffolds, an efficient method, employing 2-aminoaryl N-monosubstituted hydrazones and 2-oxo-3-butenoates under Brønsted acid catalysis, has been developed. This strategy highlights the umpolung reactivity of 2-aminobenzaldehyde arylhydrazones toward 2-oxo-3-butenoates to afford (E)-diazoaryl-benzo[b]azepine derivatives in excellent yields (89-99%) and with high diastereoselectivities (>19:1 dr).

AB - To construct multisubstituted seven-membered nitrogenous heterocyclic scaffolds, an efficient method, employing 2-aminoaryl N-monosubstituted hydrazones and 2-oxo-3-butenoates under Brønsted acid catalysis, has been developed. This strategy highlights the umpolung reactivity of 2-aminobenzaldehyde arylhydrazones toward 2-oxo-3-butenoates to afford (E)-diazoaryl-benzo[b]azepine derivatives in excellent yields (89-99%) and with high diastereoselectivities (>19:1 dr).

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ER -

Organocatalytic Diastereoselective Synthesis of Diazoaryl-benzo[b]azepine Derivatives

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 1940881: Experimental Crystal Structure Determination

引用此