메뉴 건너뛰기




Volumn 128, Issue 37, 2006, Pages 12062-12063

Synthesis of indenyl ethers by gold(I)-catalyzed intramolecular carboalkoxylation of alkynes

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; ETHER DERIVATIVE; GOLD; INDENE DERIVATIVE; INDENYL ETHER; UNCLASSIFIED DRUG;

EID: 33748774422     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja064209+     Document Type: Article
Times cited : (196)

References (47)
  • 28
    • 33748770587 scopus 로고    scopus 로고
    • note
    • 3e (1 atm) at 80 °C in toluene afforded 2a in 91% yield; however, under identical conditions, a complex mixture was formed in the reaction of 1k. For additional catalysts examined, see Supporting Information.
  • 29
    • 33748760297 scopus 로고    scopus 로고
    • note
    • Other solvents produced lower yields of cyclized products: toluene, 22%; THF, 0%; acetonitrile, 21%; nitromethane, 6%.
  • 38
    • 0041407526 scopus 로고    scopus 로고
    • Enantioenriched ethers were prepared from the corresponding alcohols prepared according to 1k and 1l: (a) Frantz, D. E.; Fässler, R.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 1806
    • Frantz, D.E.1    Fässler, R.2    Carreira, E.M.3
  • 41
    • 33748800691 scopus 로고    scopus 로고
    • note
    • The absolute configuration of 21 was assigned using the mandelate ester method on alcohol 15 (see Supporting Information).
  • 42
    • 33748778186 scopus 로고    scopus 로고
    • note
    • Reaction of enantioenriched ether 1c (89% ee) gave nearly racemic indenyl ether 2c (9% ee). Similarly, almost racemic 2c was observed at 50% conversion, while 1c was recovered without substantial racemization.
  • 43
    • 33748806275 scopus 로고    scopus 로고
    • note
    • A mechanism involving anti-addition of an alkyne nucleophile to an allyl or arene-gold(1) complex (as proposed for Pd in ref 7b) would also account for the observed overall inversion. However, this mechanism is not consistent with the observation that, under identical conditions, styrene 16 was recovered unreacted.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.