메뉴 건너뛰기




Volumn 129, Issue 44, 2007, Pages 13410-13411

Catalytic asymmetric cyclopropanation of enones with dimethyloxosulfonium methylide promoted by a La-Li3-(Biphenyldiolate)3 + NaI complex

Author keywords

[No Author keywords available]

Indexed keywords

BIPHENYL DERIVATIVE; BIPHENYLDIOLATE; DIMETHYLOXOSULFONIUM METHYLIDE; ENONE DERIVATIVE; KETONE DERIVATIVE; LANTHANIDE; LITHIUM; LITHIUM DERIVATIVE; SODIUM IODIDE; SULFONIUM DERIVATIVE; UNCLASSIFIED DRUG;

EID: 35948949568     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja076797c     Document Type: Article
Times cited : (99)

References (32)
  • 1
    • 0038222536 scopus 로고    scopus 로고
    • A review of stereoselective cyclopropanations: Lebel, H.; Marcoux, J.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
    • A review of stereoselective cyclopropanations: Lebel, H.; Marcoux, J.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
  • 3
    • 0032482059 scopus 로고    scopus 로고
    • For selected recent examples with high ee, see Simmons-Smith type: (a) Denmark, S. E.; O'Connor, S. P.; Wilson, S. R. Angew. Chem., Int. Ed. 1998, 37, 1149.
    • For selected recent examples with high ee, see Simmons-Smith type: (a) Denmark, S. E.; O'Connor, S. P.; Wilson, S. R. Angew. Chem., Int. Ed. 1998, 37, 1149.
  • 5
    • 85008090337 scopus 로고    scopus 로고
    • Metallocarbenoid-mediated reaction: (c) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726.
    • Metallocarbenoid-mediated reaction: (c) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726.
  • 9
    • 0035901642 scopus 로고    scopus 로고
    • Catalytic generation of chiral ylides: (a) Aggarwal, V. K.; Alonso, E.; Fang, G. Y.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433 and references therein.
    • Catalytic generation of chiral ylides: (a) Aggarwal, V. K.; Alonso, E.; Fang, G. Y.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433 and references therein.
  • 11
    • 14944346768 scopus 로고    scopus 로고
    • Catalytic activation of electrophiles: (a) Kunz R. K.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 3240.
    • Catalytic activation of electrophiles: (a) Kunz R. K.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 3240.
  • 14
    • 0033612173 scopus 로고    scopus 로고
    • For other organocatalytic approach, see also (a) Arai, S.; Nakayama, K.; Ishida, T.; Shioiri, T. Tetrahedron Lett. 1999, 40, 4215.
    • For other organocatalytic approach, see also (a) Arai, S.; Nakayama, K.; Ishida, T.; Shioiri, T. Tetrahedron Lett. 1999, 40, 4215.
  • 17
    • 0034684524 scopus 로고    scopus 로고
    • With stoichiometric amount of Lewis acids and a chiral ligand: Mamai, A, Madalengoitia, J. S. Tetrahedron Lett. 2000, 41, 9009
    • With stoichiometric amount of Lewis acids and a chiral ligand: Mamai, A.; Madalengoitia, J. S. Tetrahedron Lett. 2000, 41, 9009.
  • 18
    • 0036625219 scopus 로고    scopus 로고
    • Review of heterobimetallic rare earth-alkali metal-BINOL complexes: Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187.
    • Review of heterobimetallic rare earth-alkali metal-BINOL complexes: Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187.
  • 19
    • 0008757162 scopus 로고    scopus 로고
    • 2: (a) Harada, T.; Tuyet, T. M. T.; Oku, A. Org. Lett. 2000, 2, 1319.
    • 2: (a) Harada, T.; Tuyet, T. M. T.; Oku, A. Org. Lett. 2000, 2, 1319.
  • 20
    • 34248189099 scopus 로고    scopus 로고
    • Utility of biphenyldiols as rare earth metal complexes: (b) Kakei, H.; Tsuji, R.; Ohshima, T.; Morimoto, H.; Matsunaga, S.; Shibasaki, M. Chem. Asian J. 2007, 2, 257 and references therein.
    • Utility of biphenyldiols as rare earth metal complexes: (b) Kakei, H.; Tsuji, R.; Ohshima, T.; Morimoto, H.; Matsunaga, S.; Shibasaki, M. Chem. Asian J. 2007, 2, 257 and references therein.
  • 22
    • 34548154771 scopus 로고    scopus 로고
    • Use as alkaline earth metal complex: (d) Yamaguchi, A.; Aoyama, N.; Matsunaga, S.; Shibasaki, M. Org. Lett. 2007, 9, 3387.
    • Use as alkaline earth metal complex: (d) Yamaguchi, A.; Aoyama, N.; Matsunaga, S.; Shibasaki, M. Org. Lett. 2007, 9, 3387.
  • 23
    • 2942635094 scopus 로고    scopus 로고
    • Utility of α,β-unsaturated N-acylpyrrole as an ester surrogate: Matsunaga, S.; Kinoshita, T.; Okada, S.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 7559 and references therein.
    • Utility of α,β-unsaturated N-acylpyrrole as an ester surrogate: Matsunaga, S.; Kinoshita, T.; Okada, S.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 7559 and references therein.
  • 24
    • 35948949422 scopus 로고    scopus 로고
    • For more detailed results and discussion of the NaI and LiI effects, see Supporting Information
    • For more detailed results and discussion of the NaI and LiI effects, see Supporting Information.
  • 25
    • 35948958136 scopus 로고    scopus 로고
    • + were observed (see Supporting Information).
    • + were observed (see Supporting Information).
  • 26
    • 35948988444 scopus 로고    scopus 로고
    • - would not be so important in this system.
    • - would not be so important in this system.
  • 27
    • 11944252146 scopus 로고    scopus 로고
    • 3 complex in asymmetric 1,4-addition reaction.(a) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194.
    • 3 complex in asymmetric 1,4-addition reaction.(a) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194.
  • 28
    • 34548159259 scopus 로고    scopus 로고
    • For recent studies on the effects of alkali metals, see: (b) Wooten, A. J.; Carroll, P. J.; Walsh, P. J. Org. Lett. 2007, 9, 3359. See also, a review in ref 8.
    • For recent studies on the effects of alkali metals, see: (b) Wooten, A. J.; Carroll, P. J.; Walsh, P. J. Org. Lett. 2007, 9, 3359. See also, a review in ref 8.
  • 29
    • 85215328951 scopus 로고    scopus 로고
    • For structural analysis of heterobimetallic rare earth-alkali metal-BINOL complexes, see a review in ref 7. See also: (a) Aspinall, H. C.; Bickley, J. F.; Dwyer, J. L. M.; Greeves, N.; Kelly, R. V.; Steiner, A. Organometallics 2000, 19, 5416.
    • For structural analysis of heterobimetallic rare earth-alkali metal-BINOL complexes, see a review in ref 7. See also: (a) Aspinall, H. C.; Bickley, J. F.; Dwyer, J. L. M.; Greeves, N.; Kelly, R. V.; Steiner, A. Organometallics 2000, 19, 5416.
  • 32
    • 25444512653 scopus 로고    scopus 로고
    • Although any proposed reaction mechanism is speculative at present, there are two possibilities. One is simple Lewis acid-accelerated mechanism, and the other mechanism is dual control of both enone 3 and ylide 2 by the La-Li3-(1b)3, NaI complex. Similar dual control mechanism is proposed by MacMillan see ref 5a, Interaction of ylide 2 with catalyst might be operative through oxygen atom of ylide 2 in the latter case. Mechanistic aspects of the present reaction will be reported in due course as a full article. We proposed related dual control mechanism in aza-Michael reaction of alkoxylamines: Yamagiwa, N, Qin, H, Matsunaga, S, Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 13419
    • 3 + NaI complex. Similar dual control mechanism is proposed by MacMillan (see ref 5a). Interaction of ylide 2 with catalyst might be operative through oxygen atom of ylide 2 in the latter case. Mechanistic aspects of the present reaction will be reported in due course as a full article. We proposed related dual control mechanism in aza-Michael reaction of alkoxylamines: Yamagiwa, N.; Qin, H.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 13419.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.