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Volumn 6, Issue 11, 1995, Pages 2613-2636

The rational design and systematic analysis of asymmetric aldol reactions using enol borinates: Applications of transition state computer modelling

Author keywords

[No Author keywords available]

Indexed keywords

KETONE;

EID: 0028853930     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/0957-4166(95)00343-N     Document Type: Review
Times cited : (70)

References (59)
  • 7
    • 84914091787 scopus 로고    scopus 로고
    • The colour pictures reproduced in Figures 1–8 can be viewed and manipulated as hyperactive molecules on the World Wide Web
  • 8
    • 84914091786 scopus 로고    scopus 로고
  • 13
    • 0011464872 scopus 로고
    • Theoretical studies of aldol stereoselectivity: the development of a force field model for enol borinates and the investigation of chiral enolate .pi.-face selectivity
    • (1990) The Journal of Organic Chemistry , vol.55 , pp. 3295
    • Li1    Paddon-Row2    Houk3
  • 18
    • 84914091785 scopus 로고    scopus 로고
    • (a) The search for the low energy conformations was run using either the Still-Chang-Guida usage directed torsional Monte Carlo search (ref 12b), the Batchmin programme (ref 12c) or the Multiconformer submode (ref 12d) of MacroModel (ref 10). (b) Chang, G.; Guida, W. C.; Still, W. C. J. Am. Chem. Soc. 1989, 111, 4379. (c) BATCHMIN is the non interactive modelling program connected to MacroModel. Version 3.1 was used on a Silicon Graphics Iris 4D-20 workstation. (d) Lipton, M.; Still, W. C. J. Comp. Chem. 1988, 9, 343.
  • 31
    • 0001620385 scopus 로고
    • New methods and strategies for the stereocontrolled synthesis of polypropionate-derived natural products
    • (1992) Pure and Applied Chemistry , vol.64 , pp. 1821
    • Paterson1
  • 33
    • 49949128203 scopus 로고
    • Torsional strain involving partial bonds. The stereochemistry of the lithium aluminium hydride reduction of some simple open-chain ketones
    • (1968) Tetrahedron Letters , pp. 2199
    • Chérest1    Felkin2    Prudent3
  • 35
    • 84914091783 scopus 로고    scopus 로고
    • (a) The first examples of the “anti-Felkin” reactions of a Z-crotylboronate with an α-methyl chiral aldehyde were presented by Hoffmann in 1980 (ref 23b). A rationale for the observed stereoselectivity, which involves the minimization of (+/−) double gauche pentane interactions in the competing cyclic, chairlike transition states, was originally proposed by Evans in 1982 (ref 1c), and discussed in detail by Hoffmann [allylboronates (ref 23c-e)] and Roush [allylboronates (ref 23f,g), aldol reactions (ref 24)]. (b) Hoffmann, R. W.; Zeiss, H.-J. Angew. Chem., Int. Ed. Engl. 1980, 19, 218. (c) Hoffmann, R. W.; Brinkmann, H.; Frenking, G. Chem. Ber. 1990, 123, 2387. (d) Brinkmann, H.; Hoffmann, R. W. Chem. Ber. 1990, 123, 2395. (e) Hoffmann, R. W.; Weidmann, U. Chem. Ber. 1985, 118, 3966. (f) Roush, W. R.; Adam, M. A.; Walts, A. E.; Harris, D. J. J. Am. Chem.Soc. 1986, 108, 3422. (g) Roush, W. R.; Walts, A. E. Tetrahedron Lett. 1985, 26, 3427.


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