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Volumn , Issue 8, 2007, Pages 1251-1260

Enantioselective intramolecular copper-catalyzed aziridination of sulfamates

Author keywords

Asymmetric catalysis; Aziridine; Copper; Nitrene; Ring opening

Indexed keywords

AZIRIDINATION; AZIRIDINES; SULFAMATES;

EID: 34247631815     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-965987     Document Type: Article
Times cited : (57)

References (70)
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    • Rhodium-catalyzed nitrene transfer has found application in total synthesis in the field of C-H amination. Impressive examples of syntheses of highly complex natural products are reported in the following articles: (a) Hinman, A, Du Bois, J. J. Am. Chem. Soc. 2003, 125, 11510
    • Rhodium-catalyzed nitrene transfer has found application in total synthesis in the field of C-H amination. Impressive examples of syntheses of highly complex natural products are reported in the following articles: (a) Hinman, A.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 11510.
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    • At this stage of the experimental work, preliminary investigations of the nucleophilic ring opening of aziridine 4a with benzylamine revealed that it occurs without loss of stereochemical information. No trace of the cis-isomer of the aziridine ring-opened product was observed, while the ee of the latter matched the ee of the aziridine 4a. According to subsequent experiments (vide infra) and Du Bois's work see ref. 13f, the reaction is believed to occur by an SN2 process. This result was used to derivatize aziridines 4b-j by reaction with benzylamine in order to determine the enantioselectivity of the asymmetric intramolecular aziridination of sulfamates 2b-j
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.