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Volumn 128, Issue 41, 2006, Pages 13368-13369

Highly enantioselective transfer hydrogenation of α,β- unsaturated ketones

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID; IMIDAZOLE DERIVATIVE; KETONE DERIVATIVE;

EID: 33750084396     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja065708d     Document Type: Article
Times cited : (373)

References (33)
  • 12
    • 33750035632 scopus 로고    scopus 로고
    • (BASF AG, Germany) PCT Int. Appl. WO2006040096, 2006
    • (d) Jaekel, C.; Paciello, R. (BASF AG, Germany) PCT Int. Appl. WO2006040096, 2006.
    • Jaekel, C.1    Paciello, R.2
  • 20
    • 33750048291 scopus 로고    scopus 로고
    • note
    • Using MacMillan catalysts (2S,5S)-(-)-2-tert-butyl-3-methyl-5-benzyl-4- oxoimidazolidinium trifluoroacetate (3j) and (S)-2-(tert-butyl)-3-methyl-4- oxoimidazolidinium trifluoroacetate (3k), respectively, under the reaction conditions described in Table I, (R)-3-methylcyclohexanone was formed with low conversions (<30%) and enantioselectivities (<57:43 er). Higher conversion (40%) and enantioselectivity (75:25 er) was obtained with (2S,5S)-5-benzyl-3- methyl-2-(5-methyl-2-furyl)-4-oxoimidazolidinium trifluoroacetate (31), which has previously been used with enone substrates (see ref 4).
  • 21
    • 33749516633 scopus 로고    scopus 로고
    • After the acceptance of this manuscript a related report in which catalyst 31 (20 mol%) has been successfully used for the transfer hydrogenation of cyclic ketones appeared. See: Tuttle, J. B.; Quellet, S. G.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 12662-12663.
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 12662-12663
    • Tuttle, J.B.1    Quellet, S.G.2    MacMillan, D.W.C.3
  • 22
    • 23044486704 scopus 로고    scopus 로고
    • For pioneering use of primary amine salts in asymmetric iminium catalysis involving aldehyde substrates, see: (a) Ishihara, K.; Nakano, K. J. Am. Chem. Soc. 2005, 127, 10504-10505.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 10504-10505
    • Ishihara, K.1    Nakano, K.2
  • 24
    • 8944249371 scopus 로고
    • For the use of preformed imines of α,β-unsaturated aldehydes and amino acid esters in diastereoselective Michael additions, see: (c) Hashimoto, S.; Komeshima, N.; Yamada, S.; Koga, K. Tetrahedron Lett. 1977, 33, 2907-2908.
    • (1977) Tetrahedron Lett. , vol.33 , pp. 2907-2908
    • Hashimoto, S.1    Komeshima, N.2    Yamada, S.3    Koga, K.4
  • 33
    • 33750087104 scopus 로고    scopus 로고
    • note
    • TRIP: 3,3′-bis(2,4,6-triisopropylphenyl)-1,1′-binaphthyl-2, 2′-diyl hydrogen phosphate.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.