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Volumn 13, Issue 24, 2011, Pages 6456-6459

Scope and mechanistic studies of electrophilic alkoxyetherification

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Indexed keywords


EID: 84055213994     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202751s     Document Type: Article
Times cited : (29)

References (55)
  • 26
    • 84055221470 scopus 로고    scopus 로고
    • We have briefly investigated using less THF, i.e., using THF as a stoichiometric reagent instead of a solvent. However, the results were not satisfactory. For details, see the Supporting Information
    • We have briefly investigated using less THF, i.e., using THF as a stoichiometric reagent instead of a solvent. However, the results were not satisfactory. For details, see the Supporting Information.
  • 30
    • 84055187091 scopus 로고    scopus 로고
    • When using salicyclic acid
    • When using salicyclic acid
  • 31
    • 84055221471 scopus 로고    scopus 로고
    • the corresponding 3,5-dibromosalicyclic adduct was obtained as the sole product. Identical result was observed when using 3,5-diromosalicyclic acid
    • (1n), the corresponding 3,5-dibromosalicyclic adduct was obtained as the sole product. Identical result was observed when using 3,5-diromosalicyclic acid
  • 32
    • 84055187126 scopus 로고    scopus 로고
    • as the nucleophlic partner
    • (o) as the nucleophlic partner.
  • 33
    • 84055180988 scopus 로고    scopus 로고
    • 4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography to yield the corresponding product
    • 4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography to yield the corresponding product.
  • 34
    • 84055180987 scopus 로고    scopus 로고
    • For the reactions that used acids 11 and 1m (Table 2, entries 11 and 12; Table 3, entries 1 and 2; Table 4), the products existed as diastereoisomeric mixtures
    • For the reactions that used acids 11 and 1m (Table 2, entries 11 and 12; Table 3, entries 1 and 2; Table 4), the products existed as diastereoisomeric mixtures.
  • 35
    • 84055221468 scopus 로고    scopus 로고
    • The carboxylic acids with neighboring hydroxyl groups (acids 1k, 1l, 1n, and 1o) returned high reaction yields; for acid 1l, removing (Table 2, entry 11 vs 8) or masking (Table 2, entry 11 vs 12) the hydroxyl group gave a lower yield. The hydroxyl group seemed could enhance the acidity of the carboxylic acid, potentially through an intramolecular hydrogen bonding (Table 2, entry 1 vs 13; 8 vs 11
    • The carboxylic acids with neighboring hydroxyl groups (acids 1k, 1l, 1n, and 1o) returned high reaction yields; for acid 1l, removing (Table 2, entry 11 vs 8) or masking (Table 2, entry 11 vs 12) the hydroxyl group gave a lower yield. The hydroxyl group seemed could enhance the acidity of the carboxylic acid, potentially through an intramolecular hydrogen bonding (Table 2, entry 1 vs 13; 8 vs 11).
  • 36
    • 84055187127 scopus 로고    scopus 로고
    • The details appear in the Supporting Information
    • The details appear in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.