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Volumn 55, Issue 16, 1999, Pages 4955-4968

A one-flask synthesis of dihydronaphthalenemethanols by directed addition of organolithium reagents to BHA naphthalenecarboxylates

Author keywords

Addition reactions; Esters; Ketene; Naphthalenes

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; ESTER; KETENE DERIVATIVE; METHANOL; METHYL IODIDE; NAPHTHALENE DERIVATIVE; ORGANOLITHIUM COMPOUND;

EID: 0033574581     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00181-7     Document Type: Article
Times cited : (35)

References (41)
  • 5
    • 0029827163 scopus 로고    scopus 로고
    • Interesting 1,6-addition of lithium amides has been reported. (a) Shimano, M.; Meyers, A. I. J. Org. Chem. 1996, 61, 5714-5715.
    • (1996) J. Org. Chem. , vol.61 , pp. 5714-5715
    • Shimano, M.1    Meyers, A.I.2
  • 10
    • 5244362549 scopus 로고    scopus 로고
    • and references cited therein
    • The reaction of arene-chromium complex has been reported. Amurrio, D.; Khan, K.; Kündig, E. P. J. Org. Chem. 1996, 61, 2258-2259, and references cited therein.
    • (1996) J. Org. Chem. , vol.61 , pp. 2258-2259
    • Amurrio, D.1    Khan, K.2    Kündig, E.P.3
  • 13
    • 0031070786 scopus 로고    scopus 로고
    • Application of the bulky ester in the nucleophilic aromatic substitution reaction has been extensively studied by Miyano. A review: Hattori, T.; Miyano, S. J. Synth. Org. Chem. 1997, 55, 121-131. Leading reference: Hattori, T.; Komuro, Y.; Hayashizaka, N.; Takahashi, H.; Miyano, S. Enantiomer 1997, 2, 203-213.
    • (1997) J. Synth. Org. Chem. , vol.55 , pp. 121-131
    • Hattori, T.1    Miyano, S.2
  • 14
    • 0030794543 scopus 로고    scopus 로고
    • Application of the bulky ester in the nucleophilic aromatic substitution reaction has been extensively studied by Miyano. A review: Hattori, T.; Miyano, S. J. Synth. Org. Chem. 1997, 55, 121-131. Leading reference: Hattori, T.; Komuro, Y.; Hayashizaka, N.; Takahashi, H.; Miyano, S. Enantiomer 1997, 2, 203-213.
    • (1997) Enantiomer , vol.2 , pp. 203-213
    • Hattori, T.1    Komuro, Y.2    Hayashizaka, N.3    Takahashi, H.4    Miyano, S.5
  • 24
    • 0013531553 scopus 로고    scopus 로고
    • note
    • Epimerization of cis-4 into trans-4 was easily carried out by treating cis-4 with sodium methoxide in THF-methanol at rt.
  • 32
    • 0013489368 scopus 로고    scopus 로고
    • note
    • Concomitant addition of methanol and sodium borohydride to the reaction mixture gave cis- and trans- 20b in 23% and 55% yields.
  • 33
    • 0002586622 scopus 로고
    • Actual metal species, lithium- or borane enolate, or ate complexes shown in 18, are not clear. The lithium enolates have been proposed not to form the corresponding enoxytrialkylborates. Negishi, E.; Idacavage, M. J. Tetrahedron Lett. 1979, 845-848.
    • (1979) Tetrahedron Lett. , pp. 845-848
    • Negishi, E.1    Idacavage, M.J.2
  • 34
    • 0013494742 scopus 로고    scopus 로고
    • Isolation of the aldehyde caused a decreased yield, probably due to its instability
    • Isolation of the aldehyde caused a decreased yield, probably due to its instability.
  • 35
    • 0013489868 scopus 로고    scopus 로고
    • Methylation of 21 also gave the product alkylated at the C4 position as the major isomer
    • Methylation of 21 also gave the product alkylated at the C4 position as the major isomer.
  • 39
    • 0013494743 scopus 로고    scopus 로고
    • note
    • 4 unless otherwise noted. THF, ether, DME, and toluene were distilled from sodium benzophenone ketyl.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.