메뉴 건너뛰기




Volumn 130, Issue 50, 2008, Pages 17085-17094

A surprising mechanistic "switch" in Lewis acid activation: A bifunctional, asymmetric approach to α-hydroxy acid derivatives

Author keywords

[No Author keywords available]

Indexed keywords

BIFUNCTIONAL; BINDING MOTIFS; CARBONYL DERIVATIVES; CINCHONA ALKALOIDS; ENOLATE; ENOLATES; EXCELLENT YIELDS; HIGH YIELDS; HYDROXY ACIDS; LEWIS ACIDS; MECHANISTIC STUDIES; NMR SPECTROSCOPIES; OPENING REACTIONS; RATE OF REACTIONS;

EID: 58049221126     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja806818a     Document Type: Article
Times cited : (54)

References (61)
  • 7
    • 0035812684 scopus 로고    scopus 로고
    • Mase, T.; et al. J. Org. Chem. 2001, 66, 6775-6786.
    • (2001) J. Org. Chem , vol.66 , pp. 6775-6786
    • Mase, T.1
  • 12
    • 49049088315 scopus 로고    scopus 로고
    • Recent examples include: (a) Wen, T.; Ding, Y.; Deng, Z.; Ofwegen, L.; Proksch, P.; Lin, W. J. Nat. Prod. 2008, 71, 1133-1140.
    • Recent examples include: (a) Wen, T.; Ding, Y.; Deng, Z.; Ofwegen, L.; Proksch, P.; Lin, W. J. Nat. Prod. 2008, 71, 1133-1140.
  • 17
    • 58049210861 scopus 로고    scopus 로고
    • Coppola, G. M.; Schuster, H. F. α-Hydroxy Acids in Enantioselective Synthesis; Wiley-VCH: Weinheim, 1997.
    • (a) Coppola, G. M.; Schuster, H. F. α-Hydroxy Acids in Enantioselective Synthesis; Wiley-VCH: Weinheim, 1997.
  • 34
    • 58049204892 scopus 로고    scopus 로고
    • 10 mol% catalyst was usually employed for screening purposes. While under revison, we observed that significantly lower catalyst loadings (3 mol%) could be employed without significant erosion of ee or yield.
    • 10 mol% catalyst was usually employed for screening purposes. While under revison, we observed that significantly lower catalyst loadings (3 mol%) could be employed without significant erosion of ee or yield.
  • 39
    • 58049204893 scopus 로고    scopus 로고
    • All calculations were performed using either Spartan 2006, Wave-function, Inc. (Hartree-Fock) or Gaussian 03: IA32L-G03RevD.01 (Density Functional Theory); see Supporting Information for details.
    • All calculations were performed using either Spartan 2006, Wave-function, Inc. (Hartree-Fock) or Gaussian 03: IA32L-G03RevD.01 (Density Functional Theory); see Supporting Information for details.
  • 40
    • 58049197311 scopus 로고    scopus 로고
    • 2 complex of o-chloranil, 0.401-0.442.
    • 2 complex of o-chloranil, 0.401-0.442.
  • 42
    • 58049220762 scopus 로고    scopus 로고
    • This result was confirmed using two other stabilized ketenes
    • This result was confirmed using two other stabilized ketenes.
  • 43
    • 58049203349 scopus 로고    scopus 로고
    • The UV spectrum is normalized at each end of the depicted region
    • The UV spectrum is normalized at each end of the depicted region.
  • 47
    • 58049207260 scopus 로고    scopus 로고
    • The change in the number of particles in going from starting materials to products is the same in both cases; this is generally believed to be an approximate wash in the amount of entropy
    • The change in the number of particles in going from starting materials to products is the same in both cases; this is generally believed to be an approximate "wash" in the amount of entropy.
  • 51
    • 58049194641 scopus 로고    scopus 로고
    • For the first 18 min of the reaction, the relationship between product formation and time remains fairly linear
    • For the first 18 min of the reaction, the relationship between product formation and time remains fairly linear.
  • 60
    • 58049196176 scopus 로고    scopus 로고
    • Su, T.; Zhu, B.-Y.; Kane-Maguire, K.; Scarborough, R. M.; Zhang, P. PCT Int. Appl. 2000, 2000071510.
    • Su, T.; Zhu, B.-Y.; Kane-Maguire, K.; Scarborough, R. M.; Zhang, P. PCT Int. Appl. 2000, 2000071510.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.