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Volumn 131, Issue 25, 2009, Pages 8971-8983

Regio- and enantioselective N-allylations of imidazole, benzimidazole, and purine heterocycles catalyzed by single-component metallacyclic iridium complexes

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLATION; ALLYLATION REACTIONS; ALLYLATIONS; ALLYLIC CARBONATES; BENZIMIDAZOLE; BENZIMIDAZOLES; ENANTIOSELECTIVE; HETEROCYCLES; HETEROCYCLIC NITROGEN; HIGH ENANTIOSELECTIVITY; HIGH YIELD; IRIDIUM CATALYST; IRIDIUM COMPLEX; KINETIC STUDY; PHOSPHORAMIDITE; PHOSPHORAMIDITE LIGANDS; SINGLE COMPONENTS; UNSYMMETRICAL;

EID: 67649631306     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja902243s     Document Type: Article
Times cited : (127)

References (84)
  • 67
    • 67649598817 scopus 로고    scopus 로고
    • The absolute configuration of 8a was assigned after conversion to the corresponding methyl ether. See the Supporting Information for additional details
    • The absolute configuration of 8a was assigned after conversion to the corresponding methyl ether. See the Supporting Information for additional details.
  • 71
    • 67649610868 scopus 로고    scopus 로고
    • note
    • The reaction of 20a with 3a in the presence of 4 mol % 2b also occurred with high branched-to-linear selectivity (90:10) and enantioselectivity (92% ee). However, the N9/N7 selectivity is reduced to 83:17.
  • 72
    • 67649616777 scopus 로고    scopus 로고
    • The preference for N9-selectivity was confirmed by NMR spectroscopy (HMBC) for compound 21e. See the Supporting Information for additional details
    • The preference for N9-selectivity was confirmed by NMR spectroscopy (HMBC) for compound 21e. See the Supporting Information for additional details.
  • 82
    • 67649574434 scopus 로고    scopus 로고
    • note
    • Product ratios for competition experiments in the absence of potassium phosphate base are as follows: 18:82 (11a/28) for the competition reaction between imidazole and benzyl amine; 40:60 (11a/29) for the competition reaction between imidazole and aniline; 50:50 (11a/5a) for the competition reaction between imidazole and benzimidazole; and 30:70 (11a/21k) for the competition reaction between imidazole and bis-BOC-adenine.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.