메뉴 건너뛰기




Volumn 43, Issue 41, 2004, Pages 5507-5510

Highly enantioselective direct organocatalytic α-chlorination of ketones

Author keywords

Asymmetric catalysis; Halogenation; Homogeneous catalysis; Ketones

Indexed keywords

CATALYSTS; CHLORINATION;

EID: 8444223916     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460462     Document Type: Article
Times cited : (119)

References (51)
  • 1
    • 2942702061 scopus 로고    scopus 로고
    • For reviews on enantioselective halogenation reactions see, for example, a) H. Ibrahim, A. Togni, Chem. Commun. 2004, 1147;
    • (2004) Chem. Commun. , pp. 1147
    • Ibrahim, H.1    Togni, A.2
  • 2
    • 0001171313 scopus 로고    scopus 로고
    • b) K. Muñiz, Angew. Chem. 2001, 113, 1701; Angew. Chem. Int. Ed. 2001, 40, 1653.
    • (2001) Angew. Chem. , vol.113 , pp. 1701
    • Muñiz, K.1
  • 3
    • 0038584547 scopus 로고    scopus 로고
    • b) K. Muñiz, Angew. Chem. 2001, 113, 1701; Angew. Chem. Int. Ed. 2001, 40, 1653.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 1653
  • 10
    • 0034605873 scopus 로고    scopus 로고
    • c) L. Hintermann, A. Togni, Angew. Chem. 2000, 112, 4530; Angew. Chem. Int. Ed. 2000, 39, 4359;
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 4359
  • 14
    • 0037087518 scopus 로고    scopus 로고
    • f) S. Piana, I. Devillers, A. Togni, U. Rothlisberger, Angew. Chem. 2000, 112, 1021; Angew. Chem. Int. Ed. 2002, 41, 979;
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 979
  • 23
    • 0036260164 scopus 로고    scopus 로고
    • α-Amination of aldehydes; a) A. Bøgevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, K. A. Jørgensen, Angew. Chem. 2002, 114, 1868; Angew. Chem. Int. Ed. 2002, 41, 1790;
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 1790
  • 26
    • 0842343649 scopus 로고    scopus 로고
    • α-oxidation of aldehydes: d) G. Zhong, Angew. Chem. 2003, 115, 4379; Angew. Chem. Int. Ed. 2003, 42, 4247;
    • (2003) Angew. Chem. , vol.115 , pp. 4379
    • Zhong, G.1
  • 27
    • 0141522552 scopus 로고    scopus 로고
    • α-oxidation of aldehydes: d) G. Zhong, Angew. Chem. 2003, 115, 4379; Angew. Chem. Int. Ed. 2003, 42, 4247;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 4247
  • 31
    • 1842792133 scopus 로고    scopus 로고
    • α-oxidation of ketones: b) A. Bøgevig, H. Sundéen, A. Córdova, Angew. Chem. 2004, 116, 1129; Angew. Chem. Int. Ed. 2004, 43, 1109;
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 1109
  • 33
    • 4243057730 scopus 로고    scopus 로고
    • c) M. Hayashi, J. Yamaguchi, T. Sumaiya, M. Shoji, Angew. Chem. 2004, 116, 1132; Angew. Chem. Int. Ed. 2004, 43, 1112.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 1112
  • 34
    • 8444227536 scopus 로고    scopus 로고
    • note
    • 1H NMR investigations of the mechanism of the α-chlorination of cyclohexanone by NCS catalyzed by (1R,2R)-diphenylethylenediamine. These investigations showed that the active catalyst was the condensation product between (1R,2R)-diphenylethylenediamine and cyclohexanone (3h) and not (1R,2R)-diphenylethylenediamine.
  • 37
    • 0037429423 scopus 로고    scopus 로고
    • For other imidazolidine-catalyzed reactions see: b) N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2003, 115, 685; Angew. Chem. Int. Ed. 2003, 42, 661;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 661
  • 39
    • 0242323633 scopus 로고    scopus 로고
    • c) N. Halland, T. Hansen, K. A. Jørgensen, Angew. Chem. 2003, 115, 4955; Angew. Chem. Int. Ed. 2003, 42, 5105;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 5105
  • 41
    • 2342614099 scopus 로고    scopus 로고
    • d) N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2004, 116, 1292; Angew. Chem. Int. Ed. 2004, 43, 1272.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 1272
  • 42
    • 6044224571 scopus 로고    scopus 로고
    • For a recent example of rate acceleration of amine-catalyzed reactions by the addition of acids, see: N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. 2004, 116, 2474; Angew. Chem. Int. Ed. 2004, 43, 2420.
    • (2004) Angew. Chem. , vol.116 , pp. 2474
    • Mase, N.1    Tanaka, F.2    Barbas III, C.F.3
  • 43
    • 3042625080 scopus 로고    scopus 로고
    • For a recent example of rate acceleration of amine-catalyzed reactions by the addition of acids, see: N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. 2004, 116, 2474; Angew. Chem. Int. Ed. 2004, 43, 2420.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 2420
  • 44
    • 8444244956 scopus 로고    scopus 로고
    • note
    • We believe that acid additives promote enamine formation and suppress chlorination of the catalyst.
  • 45
    • 8444239044 scopus 로고    scopus 로고
    • note
    • 2-Nitrobenzoic acid (20 mol%) led to less than 1% conversion after 18 h in the absence of 4,5-DPI 3i in a 1:1 mixture of cyclohexanone and NCS at ambient temperature.
  • 46
    • 8444236098 scopus 로고    scopus 로고
    • note
    • Less than 1% conversion of 1e and 1f was observed in the absence of 2-nitrobenzoic acid.
  • 47
    • 8444230200 scopus 로고    scopus 로고
    • note
    • No racemization was found to occur during filtration through a short silica plug.
  • 48
    • 8444227179 scopus 로고    scopus 로고
    • note
    • 4 were required.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.