Chain extension of aldonolactones by samarium iodide mediated Dreiding- Schmidt reactions and samarium assisted Imamoto reactions

Tetrahedron

Volumn 52, Issue 29, 1996, Pages 9759-9776

  Csuk, René ^a   Höring, Ulrike ^b   Schaade, Martina ^b,c  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

^b UNIVERSITY OF HEIDELBERG   (Germany)

^c UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; ACRYLONITRILE; LACTONE; METHYL IODIDE; PROPANOL; SAMARIUM;

ARTICLE; CARBOHYDRATE SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL MODIFICATION; COMPUTER SIMULATION; DIMERIZATION; ELECTRON TRANSPORT; INFRARED SPECTROMETRY; PRECURSOR; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030586205     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00508-X     Document Type: Article

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36. 18 When these zinc-mediated reactions between the carbohydrate derived carbonyl compounds and the alkyl 2-bromomethyl-acrylate were performed under classical conditions, however, the target molecules were obtained only in low yields and mostly without any stereoselectivity; cf. Rauter, A. P.; Figueiredo, J. A.; Ismael, I.; Pais, M. S.; Gonzales, A. G.; Diaz, J.; Barrera, J. B., J. Carbohydr. Chem. 1987, 6, 259-272.
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45. 26 It seems most likely that the proximal oxygenated substituents on the carbohydrate moiety act as directing groups during the addition rather by steric effects than by chelation. As shown for the zinc-silver/graphite mediated Dreiding-Schmidt reaction spontaneous cyclization of the intermediary zinc alcoholate can trap the initially formed products (i.e. the products of a kinetically controlled reaction, cf. ref. 28). The thermodynamically more stable products are formed by subsequent anomerization reactions.
46. 27 AM1 calculations (program MOPAC version 6.0, precise option, Pulay's method in SCF, using a CAChe 3.8 environment) were performed and the calculated values of the heat of formation of the respective anomers were compared, although one should keep in mind that calculated energy differences between anomers are often overestimated; cf. Juaresti, E.; Cuevas, C., Tetrahedron 1992, 48, 5019-5087. For AM1: Dewar, M. J. J.; Zoebisch, E. G.; Healy, F. F.; Steward, J. J. P., J. Am. Chem. Soc. 1985, 107, 3902-3909.
47. 27 AM1 calculations (program MOPAC version 6.0, precise option, Pulay's method in SCF, using a CAChe 3.8 environment) were performed and the calculated values of the heat of formation of the respective anomers were compared, although one should keep in mind that calculated energy differences between anomers are often overestimated; cf. Juaresti, E.; Cuevas, C., Tetrahedron 1992, 48, 5019-5087. For AM1: Dewar, M. J. J.; Zoebisch, E. G.; Healy, F. F.; Steward, J. J. P., J. Am. Chem. Soc. 1985, 107, 3902-3909.
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51. 2 mediated Reformatsky reactions of aldonolactones with alkyl 2-bromo-alkanoates as compared to the reaction of bromoacetonitrile; cf. ref. 25
52. 31 Cohen, N.; Banner, B.L.; Laurenzano, A. J., Org. Synth. 1985, 63, 127-135.
53. 2 mediated selfcondensations: Park, H. S.; Lee, I. S.; Kim, Y. H., Tetrahedron Lett. 1995, 36, 1673-1674.
54. 33 No dimerization of the aldonolactone took place either; cf. Csuk, R.; Schaade, M.; Schmidt, A., Tetrahedron 1994, 50, 11885-11892.
55. 34 For the preparation of the starting material cf. ref. 37 and Csuk, R.; Hugener M.; Vasella, A., Helv. Chim. Acta 1988, 71, 609-618.
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57. 36 Bis-addition in Dreiding-Schmidt type reactions has previously been reported for the reaction of acid chlorides and nitriles: El Alami, N.; Belaud, C.; Villieras, J., J. Organomet. Chem. 1987, 319, 303-309.
58. 37 Previously prepared in an impure form: Regeling, H.; Chittenden, G. J. F., Recl. Trav. Chim. Pays-Bas 1989, 108, 330-334.
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