메뉴 건너뛰기




Volumn , Issue 10, 2007, Pages 1490-1500

Design versus discovery in synthetic applications of organoalanes

Author keywords

Aldehydes; Asymmetric; Catalysis; Enones; Organometallics

Indexed keywords

2,2' DIHYDROXY 1,1' BINAPHTHYL; ALDEHYDE DERIVATIVE; ALLYL COMPOUND; ALUMINUM DERIVATIVE; COPPER DERIVATIVE; HALIDE; ORGANOMETALLIC COMPOUND; REAGENT;

EID: 34347356597     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-980376     Document Type: Review
Times cited : (16)

References (76)
  • 10
    • 34347343489 scopus 로고    scopus 로고
    • Chem. Abstr. 2000, 133, 237651.
    • Chem. Abstr. 2000, 133, 237651.
  • 15
    • 34347364216 scopus 로고    scopus 로고
    • Calculations were carried out using Spartan (www.wavefun.com) for Mac '02 to generate equilibrium geometries at using the semi-empirical PM3; Chapron, A
    • unpublished results
    • Calculations were carried out using Spartan (www.wavefun.com) for Mac '02 to generate equilibrium geometries at using the semi-empirical PM3; Chapron, A. unpublished results.
  • 16
  • 21
    • 34347331950 scopus 로고    scopus 로고
    • The transition states G/H are conjectures; they could not be attained by PM3 calculation.
    • The transition states G/H are conjectures; they could not be attained by PM3 calculation.
  • 22
    • 34347355007 scopus 로고    scopus 로고
    • The enolates were prepared by the chemistry of ref. 15. Neat Ac 2O (2.5 equiv) was added and the temperature raised from -45 to +6°C over 6 h, Z, 3S)-1,3-Dimethyloct- 1-enyl Acetate 1H NMR (400.1 MHz, CDCl3, δ, 0.87 (3 H, t, J, 7.2 Hz, CH2Me, 0.91 (3 H, d, J, 6.7 Hz, CHMe, 1.19-1.39 [8 H, m, CH2) 4, 1.87 (3 H, d, J, 0.9 Hz, CMe, 2.17 (3 H, s, COMe, 2.34 (1 H, m, CHMe, 4.77 (1 H, dd, J, 9.8, 0.9 Hz, CH, Irradiation of the olefinic =CH signal (δ, 4.77 ppm) produced a 3.6% NOE at the enol methyl (δ, 1.87 ppm) consistent with a Z double-bond geometry. 13C NMR (100.6 MHz, CDCl3, δ, 15.5 (Me, 19.5 (Me, 21.1 (Me, 22.7 (CH2, 27.0 (CH2, 30.6 (CH, 32.0 (CH2, 37.2 (CH2, 123.4, CH, 143.8, COAc, 169.1 (C=0, IR CHCl
    • +]: 198.1602.
  • 26
    • 0029979566 scopus 로고    scopus 로고
    • For CuTC = Copper(I) thiophene-2-carboxylate, see: Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748.
    • For CuTC = Copper(I) thiophene-2-carboxylate, see: Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748.
  • 52
    • 34347358166 scopus 로고    scopus 로고
    • I am indebted to Prof. D. Gillheany (UCD, Ireland) for this advice; he assures me it arose in the K. B. Sharpless group in the 1990s. It's not always true, but is commonly observed.
    • I am indebted to Prof. D. Gillheany (UCD, Ireland) for this advice; he assures me it arose in the K. B. Sharpless group in the 1990s. It's not always true, but is commonly observed.
  • 57
    • 0012831492 scopus 로고    scopus 로고
    • 3Al·(quinuclidine) (TMQUAL). See also: Schumann, H.; Wassermann, B. C.; Schutte, S.; Heymer, B.; Nickel, S.; Seuß, T. D.; Wernik, S.; Demtshuk, J.; Girgsdies, F.; Wiemann, R. Z. Anorg. Allg. Chem. 2000, 626, 2081; and references therein.
    • 3Al·(quinuclidine) (TMQUAL). See also: Schumann, H.; Wassermann, B. C.; Schutte, S.; Heymer, B.; Nickel, S.; Seuß, T. D.; Wernik, S.; Demtshuk, J.; Girgsdies, F.; Wiemann, R. Z. Anorg. Allg. Chem. 2000, 626, 2081; and references therein.
  • 64
    • 34347329825 scopus 로고    scopus 로고
    • My sincere thanks to both Charles Davis (of Sigma-Aldrich) and John Blacker (at NPILPharma) for their advice and insights into the world of commercial chemistry. DABAL is now available from Sigma-Aldrich (catalogue no. 68210-1 DABAL-trimethylaluminium).
    • My sincere thanks to both Charles Davis (of Sigma-Aldrich) and John Blacker (at NPILPharma) for their advice and insights into the world of commercial chemistry. DABAL is now available from Sigma-Aldrich (catalogue no. 68210-1 DABAL-trimethylaluminium).
  • 69
    • 6844254916 scopus 로고    scopus 로고
    • Reviews of Pd-catalysed allylation: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
    • Reviews of Pd-catalysed allylation: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.