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Volumn 48, Issue 28, 2009, Pages 5121-5124

Enantioselective linchpin catalysis by SOMO catalysis: An approach to the asymmetric a-chlorination of aldehydes and terminal epoxide formation

Author keywords

Enantioselectivity asymmetric catalysis; Epoxidation ; Organocatalysis

Indexed keywords

ENANTIOSELECTIVE; NEW APPROACHES; ORGANOCATALYSIS; SINGLY OCCUPIED MOLECULAR ORBITALS; TERMINAL EPOXIDE;

EID: 70349904562     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200901855     Document Type: Article
Times cited : (174)

References (44)
  • 1
    • 0003445429 scopus 로고    scopus 로고
    • Vols, Eds, E.N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Berlin
    • a) Comprehensive Asymmetric Catalysis, Vols. 1-3 (Eds.: E.N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999;
    • (1999) Comprehensive Asymmetric Catalysis , vol.1-3
  • 2
    • 0000585313 scopus 로고    scopus 로고
    • Eds, E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Berlin
    • b) Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 2004, Supplement 1 - 2.
    • (2004) Comprehensive Asymmetric Catalysis , Issue.SUPPL.EMENT 1 , pp. 2
  • 3
    • 36149001272 scopus 로고    scopus 로고
    • For pioneering work on transition-metal-mediated linchpin catalysis, see
    • For pioneering work on transition-metal-mediated linchpin catalysis, see: H. E. Burks, X P. Morken, Chem. Commun. 2007, 4717.
    • (2007) Chem. Commun , pp. 4717
    • Burks, H.E.1    Morken, X.P.2
  • 7
    • 70349952916 scopus 로고    scopus 로고
    • N. De Kimpe, R. Verhé in The Chemistry of a-Haloketones, aHaloaldehydes and a-Haloimines (Eds. : S. Patai, Z. Rappoport), Wiley, Chichester, 1988.
    • N. De Kimpe, R. Verhé in The Chemistry of a-Haloketones, aHaloaldehydes and a-Haloimines (Eds. : S. Patai, Z. Rappoport), Wiley, Chichester, 1988.
  • 8
    • 70349953720 scopus 로고    scopus 로고
    • Reviews and recent examples of enantioselective a-chlorinations
    • Reviews and recent examples of enantioselective a-chlorinations:
  • 18
    • 70349938455 scopus 로고    scopus 로고
    • While it has been established that aldehydes can be converted into epoxides, a-amino acids etc, over several discrete steps (see references [11a-d, linchpin catalysis provides a strategy that enables the direct in situ conversion of simple aldehydes into these valuable synthons (in one reaction vessel) without the isolation or purification of the intermediate
    • While it has been established that aldehydes can be converted into epoxides, a-amino acids etc., over several discrete steps (see references [11a-d]), linchpin catalysis provides a strategy that enables the direct in situ conversion of simple aldehydes into these valuable synthons (in one reaction vessel) without the isolation or purification of the intermediate.
  • 23
    • 70349947768 scopus 로고    scopus 로고
    • Hydrolytic kinetic resolution
    • Hydrolytic kinetic resolution:
  • 26
    • 1042265088 scopus 로고    scopus 로고
    • L. P. C Nielsen, C P. Stevenson, D. G. Blackmond, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 1360. Organocatalytic epoxidation of styrenes:
    • c) L. P. C Nielsen, C P. Stevenson, D. G. Blackmond, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 1360. Organocatalytic epoxidation of styrenes:
  • 27
    • 70349963400 scopus 로고    scopus 로고
    • H. Tian, J.. She, J.. Jiaxi, Y. Shi, Org. Lett. 2001, 5, 1929;
    • d) H. Tian, J.. She, J.. Jiaxi, Y. Shi, Org. Lett. 2001, 5, 1929;
  • 28
    • 0037134199 scopus 로고    scopus 로고
    • H. Tian, J.. She, H. Yu, L. Shu, Y. Shi, J. Org. Chem. 2002, 67, 2435.
    • e) H. Tian, J.. She, H. Yu, L. Shu, Y. Shi, J. Org. Chem. 2002, 67, 2435.
  • 29
    • 70349960430 scopus 로고    scopus 로고
    • Organocatalytic epoxidation of a,ß-unsaturated carbonyls, see
    • Organocatalytic epoxidation of a,ß-unsaturated carbonyls, see:
  • 32
    • 70349953714 scopus 로고    scopus 로고
    • -1), $0.27 (based on SigmaAldrich or Acros Organics pricing for 2009).
    • -1), $0.27 (based on SigmaAldrich or Acros Organics pricing for 2009).
  • 34
    • 1842863015 scopus 로고    scopus 로고
    • N. Halland, A. Braunton, S. Bachmann, M. Marigo, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 4790;
    • b) N. Halland, A. Braunton, S. Bachmann, M. Marigo, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 4790;
  • 39
    • 7044286458 scopus 로고    scopus 로고
    • LiCl in oxidative cyclizations: B. B. Snider, Chem. Rev. 1996, 96, 339.
    • LiCl in oxidative cyclizations: B. B. Snider, Chem. Rev. 1996, 96, 339.
  • 40
    • 53349122064 scopus 로고    scopus 로고
    • The capability of 2 to catalyze photoredox enamine transformations at room temperature has already been shown: D. A. Nicewicz, D. W. C. MacMillan, Science 2008, 322, 77.
    • The capability of 2 to catalyze photoredox enamine transformations at room temperature has already been shown: D. A. Nicewicz, D. W. C. MacMillan, Science 2008, 322, 77.
  • 41
    • 70349955363 scopus 로고    scopus 로고
    • DFT calculations performed using B3LYP/6-311 + G(2d,p)// B3LYP/6-31G(d).
    • DFT calculations performed using B3LYP/6-311 + G(2d,p)// B3LYP/6-31G(d).
  • 42
    • 70349968692 scopus 로고    scopus 로고
    • 2O.
    • 2O.
  • 43
    • 70349956952 scopus 로고    scopus 로고
    • See the Supporting Information for details
    • See the Supporting Information for details.
  • 44
    • 0000247876 scopus 로고
    • For pioneering work on the mechanism, of radical species in the presence of copper salts, see
    • For pioneering work on the mechanism, of radical species in the presence of copper salts, see: J. K. Kochi, Acc. Chem. Res. 1974, 7, 351.
    • (1974) Acc. Chem. Res , vol.7 , pp. 351
    • Kochi, J.K.1


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