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Volumn 10, Issue 19, 2004, Pages 4790-4797

Enantioselective cyanosilylation of ketones by a catalytic double-activation method with an aluminium complex and an N-oxide

Author keywords

Asymmetric catalysis; Cyanohydrins; Double activation; Enantioselectivity; Ketones

Indexed keywords

CATALYSIS; CATALYST ACTIVITY; COMPLEXATION; NITROGEN OXIDES;

EID: 5444236257     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400506     Document Type: Article
Times cited : (111)

References (75)
  • 1
    • 0142194987 scopus 로고    scopus 로고
    • For reviews on the enantioselective construction of quaternary stereocenters, see. a) J. Christoffers, A. Baro, Angew. Chem 2003, 115, 1726-1728; Angew Chem Int Ed 2003, 42, 1688-1690,
    • (2003) Angew Chem , vol.115 , pp. 1726-1728
    • Christoffers, J.1    Baro, A.2
  • 2
    • 0037541354 scopus 로고    scopus 로고
    • For reviews on the enantioselective construction of quaternary stereocenters, see. a) J. Christoffers, A. Baro, Angew. Chem 2003, 115, 1726-1728; Angew Chem Int Ed 2003, 42, 1688-1690,
    • (2003) Angew Chem Int Ed , vol.42 , pp. 1688-1690
  • 3
    • 0001227615 scopus 로고    scopus 로고
    • b) J. Christoffers, A Mann, Angew Chem. 2001, 113, 4725-4732; Angew Chem Int Ed. 2001, 40, 4591-4597,
    • (2001) Angew Chem , vol.113 , pp. 4725-4732
    • Christoffers, J.1    Mann, A.2
  • 4
    • 0035905575 scopus 로고    scopus 로고
    • b) J. Christoffers, A Mann, Angew Chem. 2001, 113, 4725-4732; Angew Chem Int Ed. 2001, 40, 4591-4597,
    • (2001) Angew Chem Int Ed , vol.40 , pp. 4591-4597
  • 6
    • 0032473509 scopus 로고    scopus 로고
    • c) E J. Corey, A Guzman-Perez, Angew. Chem 1998, 110, 402-415, Angew Chem. Int Ed 1998, 37, 388-401,
    • (1998) Angew Chem Int Ed , vol.37 , pp. 388-401
  • 7
    • 0001521888 scopus 로고
    • d) K Fuji, Chem Rev 1993, 93, 2037-2066
    • (1993) Chem Rev , vol.93 , pp. 2037-2066
    • Fuji, K.1
  • 8
    • 0000140586 scopus 로고    scopus 로고
    • For reviews on the synthesis and applications of cyanohydrins, see a) R. J. H Gregory, Chem Rev 1999, 99, 3649-3682,
    • (1999) Chem Rev , vol.99 , pp. 3649-3682
    • Gregory, R.J.H.1
  • 9
    • 0000710861 scopus 로고
    • b) F Effenberger, Angew. Chem 1994, 106, 1609-1619; Angew Chem. Int. Ed Engl 1994, 33, 1555-1564,
    • (1994) Angew Chem , vol.106 , pp. 1609-1619
    • Effenberger, F.1
  • 10
    • 33748215202 scopus 로고
    • b) F Effenberger, Angew. Chem 1994, 106, 1609-1619; Angew Chem. Int. Ed Engl 1994, 33, 1555-1564,
    • (1994) Angew Chem Int Ed Engl , vol.33 , pp. 1555-1564
  • 11
  • 17
    • 0035905571 scopus 로고    scopus 로고
    • For reviews on bifunctional catalysis, see a) H Groger, Chem Eur J 2001, 7, 5246-5251;
    • (2001) Chem Eur J , vol.7 , pp. 5246-5251
    • Groger, H.1
  • 26
    • 0037087605 scopus 로고    scopus 로고
    • a) H Deng, M P Isler, M L Snapper, A H Hoveyda, Angew Chem 2002, 114, 1051-1054; Angew Chem Int Ed 2002, 41, 1009-1012.
    • (2002) Angew Chem Int Ed , vol.41 , pp. 1009-1012
  • 28
    • 0029764025 scopus 로고    scopus 로고
    • The dipeptide catalysts have been developed and applied to other asymmetric reactions. For examples, see b) B M Cole, K D Shimizu, C A Krueger, J. P. A Harrity, M L. Snapper, A. H Hoveyda, Angew Chem 1996, 108, 1776-1779, Angew Chem Int Ed Engl 1996, 35, 1668-1671
    • (1996) Angew Chem Int Ed Engl , vol.35 , pp. 1668-1671
  • 46
    • 0033615304 scopus 로고    scopus 로고
    • C = 17.9 ppm remaining unchanged both during the catalyst generation m the absence of TMSCN and during the reaction period, which suggested that the third Et attached to the Al atom of IkAlEt3 complex did not exchange with CN For methyl-Al-salen complex, see a) J K Myers, E N. Jacobsen, J Am Chem Soc 1999, 121, 8959-8960.
    • (1999) J Am Chem Soc , vol.121 , pp. 8959-8960
    • Myers, J.K.1    Jacobsen, E.N.2
  • 48
    • 0035128046 scopus 로고    scopus 로고
    • and references therein
    • c) D A Atwood, M J Harvey, Chem Rev 2001, 101, 37, and references therein,
    • (2001) Chem Rev , vol.101 , pp. 37
    • Atwood, D.A.1    Harvey, M.J.2
  • 50
    • 0035907043 scopus 로고    scopus 로고
    • d) D A Evans, J M Janey, N Magomedov, J S Tedrow, Angew Chem 2001, 113, 1936-1939; Angew Chem Int Ed 2001, 40, 1884-1888,
    • (2001) Angew Chem Int Ed , vol.40 , pp. 1884-1888
  • 52
    • 0037087705 scopus 로고    scopus 로고
    • e) E J Campbell, H Zhou, S. T Nguyen, Angew Chem 2002, 114, 1062-1064; Angew Chem lnt Ed 2002, 41, 1020-1022,
    • (2002) Angew Chem Lnt Ed , vol.41 , pp. 1020-1022
  • 54
    • 0042812083 scopus 로고    scopus 로고
    • f) A Baeza, J. Casas, C Najera, J M Sansano, J M Saa, Angew Chem 2003, 115, 3251-3254; Angew Chem Int Ed 2003, 42, 3143-3146,
    • (2003) Angew Chem Int Ed , vol.42 , pp. 3143-3146
  • 67
    • 0345711474 scopus 로고    scopus 로고
    • a) E M Vogl, H Groger, M Shibasaki, Angew Chem 1999, 111, 1672-1680, Angew Chem Int Ed 1999, 38, 1570-1577,
    • (1999) Angew Chem Int Ed , vol.38 , pp. 1570-1577
  • 70
    • 5444234567 scopus 로고    scopus 로고
    • note
    • H = 0.35 ppm. After it has coordinated to N-oxide 2d, however, a new signal appears at δH = 017 ppm.
  • 72
    • 5444252410 scopus 로고    scopus 로고
    • note
    • TMSCN appears to be involved in the rate-determining step because more than an equivalent quantity (2equiv) of it relative to the ketones was needed to give the optimum reaction rate and enantioselectivity
  • 74
    • 0035793293 scopus 로고    scopus 로고
    • C M Mascarenha, S P. Miller, P S White, J P Morken, Angew Chem 2001, 113, 621-623, Angew Chem. Int. Ed. 2001, 40, 601-603
    • (2001) Angew Chem Int Ed , vol.40 , pp. 601-603


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.