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Volumn 47, Issue 8, 2008, Pages 1469-1472

Enantioselective catalytic carbonyl-ene cyclization reactions

Author keywords

Aldehydes; Asymmetric catalysis; Chromium; Cyclization; Ene reaction

Indexed keywords

ALDEHYDES; CHEMICAL REACTIONS; CHROMIUM; CYCLIZATION;

EID: 39849102738     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200704439     Document Type: Article
Times cited : (65)

References (39)
  • 1
    • 0000379088 scopus 로고    scopus 로고
    • For a selection of recent reports of carbonyl-ene and related cyclizations in stereoselective syntheses of biologically active molecules, see: a B. Alcaide, C. Pardo, C. Rodriguez-Ranera, A. Rodriquez-Vicente, Org. Lett. 2001, 3, 4205-4208;
    • For a selection of recent reports of carbonyl-ene and related cyclizations in stereoselective syntheses of biologically active molecules, see: a) B. Alcaide, C. Pardo, C. Rodriguez-Ranera, A. Rodriquez-Vicente, Org. Lett. 2001, 3, 4205-4208;
  • 5
    • 0001230709 scopus 로고
    • For reviews of the ene reaction, including the carbonyl-ene reaction and cyclization, see: a
    • For reviews of the ene reaction, including the carbonyl-ene reaction and cyclization, see: a) H. M. R. Hoffmann, Angew. Chem. 1969, 81, 597-618;
    • (1969) Angew. Chem , vol.81 , pp. 597-618
    • Hoffmann, H.M.R.1
  • 11
    • 0001578082 scopus 로고    scopus 로고
    • For a review of advances in enantioselective catalytic ene reactions, see: a, Eds, E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Berlin, chap. 32.3;
    • For a review of advances in enantioselective catalytic ene reactions, see: a) K. Mikami, M. Terrada in Comprehensive Asymmetric Catalysis, Vol. 3 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, chap. 32.3;
    • (1999) Comprehensive Asymmetric Catalysis , vol.3
    • Mikami, K.1    Terrada, M.2
  • 13
    • 0001226063 scopus 로고    scopus 로고
    • For examples of enantioselective intermolecular carbonyl-ene reactions of electron-deficient aldehydes, such as chloral and fluoral, see: a K. Maruoka, Y. Hoshino, T. Shirasaka, H. Yamamoto, Tetrahedron Lett. 1988, 29, 3967-3970;
    • For examples of enantioselective intermolecular carbonyl-ene reactions of electron-deficient aldehydes, such as chloral and fluoral, see: a) K. Maruoka, Y. Hoshino, T. Shirasaka, H. Yamamoto, Tetrahedron Lett. 1988, 29, 3967-3970;
  • 15
    • 0742287187 scopus 로고    scopus 로고
    • For examples of enantioselective intermolecular carbonyl-ene reactions of glyoxalate and pyruvate derivatives, see: a K. Aikawa, S. Kainuma, M. Hatano, K. Mikami, Tetrahedron Lett. 2004, 45, 183-185;
    • For examples of enantioselective intermolecular carbonyl-ene reactions of glyoxalate and pyruvate derivatives, see: a) K. Aikawa, S. Kainuma, M. Hatano, K. Mikami, Tetrahedron Lett. 2004, 45, 183-185;
  • 27
    • 0000778829 scopus 로고    scopus 로고
    • For examples of enantioselective catalytic intermolecular carbonyl-ene reactions of unactivated aldehydes see: a E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649-3650;
    • For examples of enantioselective catalytic intermolecular carbonyl-ene reactions of unactivated aldehydes see: a) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649-3650;
  • 30
    • 0142214760 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 4771-4774.
    • (2003) Angew. Chem. Int. Ed , vol.42 , pp. 4771-4774
  • 31
    • 0000995013 scopus 로고    scopus 로고
    • For enantioselective carbonyl-ene cyclizations promoted by a more than stoichiometric amount of Zn/binol system, see: S. Sakane, K. Maruoka, H. Yamamoto, Tetrahedron 1986, 42, 2203-2209
    • For enantioselective carbonyl-ene cyclizations promoted by a more than stoichiometric amount of Zn/binol system, see: S. Sakane, K. Maruoka, H. Yamamoto, Tetrahedron 1986, 42, 2203-2209.
  • 32
    • 0026344849 scopus 로고
    • For enantioselective catalysis of carbonyl-ene cyclizations by Ti complexes, see: a
    • For enantioselective catalysis of carbonyl-ene cyclizations by Ti complexes, see: a) K. Mikami, E. Sawa, M. Terada, Tetrahedron: Asymmetry 1991, 2, 1403-1412;
    • (1991) Tetrahedron: Asymmetry , vol.2 , pp. 1403-1412
    • Mikami, K.1    Sawa, E.2    Terada, M.3
  • 34
    • 0142106406 scopus 로고    scopus 로고
    • II-catalyzed enantioselective cyclizations of α-keto esters, see: D. Yang, M. Yang, N. Zhu, Org. Lett. 2003, 5, 3749-3752.
    • II-catalyzed enantioselective cyclizations of α-keto esters, see: D. Yang, M. Yang, N. Zhu, Org. Lett. 2003, 5, 3749-3752.
  • 35
    • 0025330437 scopus 로고    scopus 로고
    • The desymmetrization of dialdehydes by ene cyclization has been investigated by Ziegler and Sobolov in an approach to the synthesis of the natural product anguidine: F. E. Ziegler, S. B. Sobolov, J. Am. Chem. Soc. 1990, 112, 2749-2758
    • The desymmetrization of dialdehydes by ene cyclization has been investigated by Ziegler and Sobolov in an approach to the synthesis of the natural product anguidine: F. E. Ziegler, S. B. Sobolov, J. Am. Chem. Soc. 1990, 112, 2749-2758.
  • 36
    • 20044390256 scopus 로고    scopus 로고
    • Intramolecular reactions of these substrates presumably also benefit from a Thorpe-Ingold effect. For a recent review, see
    • Intramolecular reactions of these substrates presumably also benefit from a Thorpe-Ingold effect. For a recent review, see: M. E. Jung, G. Piizi, Chem. Rev. 2005, 105, 1735-1766.
    • (2005) Chem. Rev , vol.105 , pp. 1735-1766
    • Jung, M.E.1    Piizi, G.2
  • 37
    • 33646403425 scopus 로고    scopus 로고
    • For a recent review of approaches to tetrahydropyran frameworks, see
    • For a recent review of approaches to tetrahydropyran frameworks, see: P. A. Clarke, S. Santos, Eur. J. Org. Chem. 2006, 2045-2053.
    • (2006) Eur. J. Org. Chem , pp. 2045-2053
    • Clarke, P.A.1    Santos, S.2
  • 38
    • 53549104363 scopus 로고    scopus 로고
    • See the Supporting Information for X-ray crystallographic data
    • See the Supporting Information for X-ray crystallographic data.
  • 39
    • 53549131210 scopus 로고    scopus 로고
    • See the Supporting Information for substrate preparation
    • See the Supporting Information for substrate preparation.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.