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Volumn 6, Issue 11, 2004, Pages 1877-1879

Use of acid fluorides increases the scope of the reductive acylation of esters

Author keywords

[No Author keywords available]

Indexed keywords

ACID; CARBOXYLIC ACID; ESTER; ETHER; FLUORIDE;

EID: 2942566675     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049333h     Document Type: Article
Times cited : (22)

References (21)
  • 8
    • 2942615644 scopus 로고    scopus 로고
    • note
    • We speculated that the low conversion is due to the bulk of this reagent. To probe this issue, we attempted the one-pot reduction/acylation with trimethylacetic anhydride, which afforded the desired product 3e in less than 30% yield under identical reaction conditions, consistent with Kiyooka's observations (ref 6), thereby supporting our conjecture.
  • 9
    • 0027465609 scopus 로고
    • Kiyooka found that increasing the bulk of the silylating reagent from TMSOTf to TBDMSOTf resulted in a poor efficiency in the reductive silylation of esters; see: Kiyooka, S.-I.; Shirouchi, M.; Kaneko, Y. Tetrahedron Lett. 1993, 34, 1491.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 1491
    • Kiyooka, S.-I.1    Shirouchi, M.2    Kaneko, Y.3
  • 11
    • 2942561205 scopus 로고    scopus 로고
    • note
    • Rychnovsky and co-workers have also noted this effect (personal communication).
  • 12
    • 2942564815 scopus 로고    scopus 로고
    • note
    • Control experiments also showed that the acylation product is stable to DIBAL-Cl under the reaction conditions.
  • 21
    • 2942594933 scopus 로고    scopus 로고
    • note
    • The use of acid fluorides simplifies the workup by avoiding emulsions, which in our hands are often observed in reactions that use anhydrides as acylation partners.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.