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Volumn 50, Issue 26, 2009, Pages 3171-3174

Highly efficient synthesis of functionalized tertiary alcohols catalyzed by potassium alkoxide-crown ether complexes

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; BRONSTED BASE; CROWN ETHER; KETONE; LEWIS BASE; POTASSIUM; POTASSIUM ALKOXIDE; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

EID: 67349180231     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.01.028     Document Type: Article
Times cited : (20)

References (49)
  • 6
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    • Pioneering Lewis acid or Lewis base catalysis with Si enolates with aldehydes:
    • Pioneering Lewis acid or Lewis base catalysis with Si enolates with aldehydes:. Mukaiyama T., Narasaka K., and Banno K. Chem. Lett. (1973) 1011
    • (1973) Chem. Lett. , pp. 1011
    • Mukaiyama, T.1    Narasaka, K.2    Banno, K.3
  • 14
    • 0037165679 scopus 로고    scopus 로고
    • 3Si enolates with ketones:
    • 3Si enolates with ketones:. Denmark S.E., and Fan Y. J. Am. Chem. Soc. 124 (2002) 4233
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 4233
    • Denmark, S.E.1    Fan, Y.2
  • 26
    • 56249148856 scopus 로고    scopus 로고
    • Very recently, Shibasaki and Matsunaga et al. used 1,2-bis(diphenylphosphoryl)benzene as a Lewis base co-catalyst in the La(III)-catalyzed diastereoselective Mannich-type reaction.
    • Very recently, Shibasaki and Matsunaga et al. used 1,2-bis(diphenylphosphoryl)benzene as a Lewis base co-catalyst in the La(III)-catalyzed diastereoselective Mannich-type reaction. Morimoto H., Yoshino T., Yukawa T., Lu G., Matsunaga S., Shibasaki M. Angew. Chem., Int. Ed. 47 (2008) 9125
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 9125
    • Morimoto, H.1    Yoshino, T.2    Yukawa, T.3    Lu, G.4    Matsunaga, S.5    Shibasaki, M.6
  • 33
    • 0001217854 scopus 로고
    • Ring opening reaction of epoxides with KCN-18-crown-6 complex:
    • Ring opening reaction of epoxides with KCN-18-crown-6 complex:. Sassaman M.B., Prakash G.K.S., and Olah G.A. J. Org. Chem. 55 (1990) 2016
    • (1990) J. Org. Chem. , vol.55 , pp. 2016
    • Sassaman, M.B.1    Prakash, G.K.S.2    Olah, G.A.3
  • 34
    • 67349128890 scopus 로고    scopus 로고
    • note
    • In this reaction, the possibility of self-catalysis by in situ generating aldolate had been denied. See Ref. 6.
  • 40
    • 67349248368 scopus 로고    scopus 로고
    • note
    • Catalyst 1 was less active than 2a or 2b. In the reaction between 3b and 16, both 17a and deprotected product 20a were obtained in 92% yield (17a:20a = ca. 4:1).
  • 41
    • 67349092749 scopus 로고    scopus 로고
    • note
    • This result was in sharp contrast to that with the Mukaiyama aldol reaction (see Table 1). Other catalysts such as KOAc-18-crown-6 and KF-18-crown-6 showed almost no reactivity under the same reaction conditions. KOPh or KOt-Bu without 18-crown-6 also showed no reactivity.
  • 46
    • 67349270834 scopus 로고    scopus 로고
    • note
    • From 20a, 3b was obtained in yields of only 19-20% in THF at 0 °C for 2 h with the use of 5 mol % of t-BuOK or 5 mol % of catalyst 2b.
  • 47
    • 67349195260 scopus 로고    scopus 로고
    • note
    • With these preliminary results to date, we cannot exclude the possibility of competitive self-catalysis by tertiary alkoxide intermediates.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.