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Volumn 43, Issue 33, 2004, Pages 4349-4352

RH-catalyzed animation of ethereal Cα-H bonds: A versatile strategy for the synthesis of complex amines

Author keywords

Animation; C H insertion; N,O acetals; Rhodium; Sulfamates

Indexed keywords

AMINATION; CATALYSIS; COMPLEXATION; MOLECULAR STRUCTURE; RHODIUM; STEREOCHEMISTRY;

EID: 4544313955     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460791     Document Type: Article
Times cited : (119)

References (35)
  • 7
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    • note
    • Compounds 2 and 3 are known generally as 1,2,3-oxathiazinane-2,2-dioxides or as 2,2-dioxotetrahydro-1,2,3-oxathiazines. We refer to such structures as oxathiazinanes or oxathiazinane N,O-acetals for convenience.
  • 8
    • 0042912996 scopus 로고    scopus 로고
    • For recent reviews on C-H amination, see: a) P. Dauban, R. H. Dodd, Synlett 2003, 1571;
    • (2003) Synlett , pp. 1571
    • Dauban, P.1    Dodd, R.H.2
  • 13
    • 33748811198 scopus 로고
    • For excellent discussions on the influence of the metal catalyst on C-H insertion reactions of carbenes, see; a) A. Padwa, D. J. Austin, Angew. Chem. 1994, 106, 1881; Angew. Chem. Int. Ed. Engl. 1994, 33, 1797;
    • (1994) Angew. Chem. , vol.106 , pp. 1881
    • Padwa, A.1    Austin, D.J.2
  • 14
    • 33748811198 scopus 로고
    • For excellent discussions on the influence of the metal catalyst on C-H insertion reactions of carbenes, see; a) A. Padwa, D. J. Austin, Angew. Chem. 1994, 106, 1881; Angew. Chem. Int. Ed. Engl. 1994, 33, 1797;
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 1797
  • 17
    • 0345791433 scopus 로고    scopus 로고
    • 4]. For a detailed account of amination reactions with chiral sulfamates, see: P. M. Wehn, J. Lee, J. Du Bois, Org. Lett. 2003, 5, 4823.
    • (2003) Org. Lett. , vol.5 , pp. 4823
    • Wehn, P.M.1    Lee, J.2    Du Bois, J.3
  • 18
    • 0002487883 scopus 로고    scopus 로고
    • For reviews on addition reactions to iminium ions, see: a) S. M. Weinreb, Top. Curr. Chem. 1997, 190, 131;
    • (1997) Top. Curr. Chem. , vol.190 , pp. 131
    • Weinreb, S.M.1
  • 21
    • 4544368595 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopy (a combination of coupling-constant and NOE data); see the Supporting Information for details.
  • 28
    • 0000000271 scopus 로고    scopus 로고
    • Addition reactions to oxocarbenium ions derived from 1,3-dioxanes may also conform to this model; see: a) S. Uehira, Z. Han, H. Shinokubo, K. Oshima, Org. Lett. 1999, 1, 1383;
    • (1999) Org. Lett. , vol.1 , pp. 1383
    • Uehira, S.1    Han, Z.2    Shinokubo, H.3    Oshima, K.4
  • 33
    • 4544245900 scopus 로고    scopus 로고
    • note
    • 3 will catalyze the addition of allyltrimethylsilane to N,O-acetals, reaction times are typically quite long (48 h), and product yields are diminished.
  • 34
    • 0035830556 scopus 로고    scopus 로고
    • Similar reaction conditions were described recently for the addition of silyl enol ethers to 2-methoxy- and 2-acyloxypiperidines; see: O. Okitsu, R. Suzuki, S. Kobayashi, J. Org. Chem. 2001, 66, 809; see also: M. Yamanaka, A. Nishida, M. Nakagawa, J. Org. Chem. 2003, 68, 3112.
    • (2001) J. Org. Chem. , vol.66 , pp. 809
    • Okitsu, O.1    Suzuki, R.2    Kobayashi, S.3
  • 35
    • 0037453552 scopus 로고    scopus 로고
    • Similar reaction conditions were described recently for the addition of silyl enol ethers to 2-methoxy- and 2-acyloxypiperidines; see: O. Okitsu, R. Suzuki, S. Kobayashi, J. Org. Chem. 2001, 66, 809; see also: M. Yamanaka, A. Nishida, M. Nakagawa, J. Org. Chem. 2003, 68, 3112.
    • (2003) J. Org. Chem. , vol.68 , pp. 3112
    • Yamanaka, M.1    Nishida, A.2    Nakagawa, M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.