Cycloaddition Reactions in Carbohydrate Chemistry by Robert M. Giuliano (Eds.)

By Robert M. Giuliano (Eds.)

content material: Cycloaddition reactions in carbohydrate chemistry : an outline / Robert M. Giuliano --
Carbohydrate dienophiles in [4 + 2] cycloadditions / Richard W. Franck --
Pyranose-derived dienes and conjugated enals : instruction and Diels-Alder cycloaddition reactions / J. Cristóbal López and Gabor Lukacs --
Synthesis of [beta]-lactams from unsaturated sugars and isocyanates / Marek Chmielewski, Zbigniew Kaluża, Jacek Grodner, and Romuald Urbański --
Diels-Alder cycloaddition to unsaturated sugars : stereocontrol as a functionality of constitution and stereochemistry / Derek Horton, Dongsoo Koh, Yasushi Takagi, and Takayuki Usui --
The [4 + 2] cycloaddition of azodicarboxylates and cyclic vinyl ethers : software to the synthesis of straightforward and complicated 2-aminosaccharides / Yves Leblanc and Marc Labelle --
Glycosylmanganese pentacarbonyl complexes : an organomanganese-based method of the synthesis of C-glycosyl derivatives / Philip DeShong, Greg A. Slough, D. Richard Sidler, Varadaraj Elango, Philip J. Rybczynski, Laura J. Smith, Thomas A. decrease, Thuy X. Le, and Gary B. Anderson --
Inter- and intramolecular Diels-Alder reactions of sugar derivatives / Pál Herczegh, Martina Zsély, László Szilágyi, István Bajza, Árpád Kovács, Gyula Batta, and Rezsö Bognár --
Carbohydrates as chiral templates in stereoselective [4 + 2] cycloaddition reactions / Horst Kunz, Bernd Müller, Waldemar Pfrengle, Karola Rück, and Wolfgang Stähle --
Aqueous cycloadditions utilizing glycoorganic substrates : stereo- and physicochemical elements / André Lubineau, Jacques Augé, Hugues Bienaymé, Nadège Lubin, and Yves Queneau --
Stereoselectivity of 1,3-dipolar cycloaddition of glycosyl nitrones to N-arylmaleimides / L. Fišera, U.A.R. Al-Timari, and P. Ertl.

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3. p. 123-125°C 20 m 39 (73%) . p. p. 123-125° C Figure 7 the benzylidene ring confers conformational rigidity to the pyranose moiety, and it is because of that conformational rigidity that only one regioisomer is obtained. Systems without the benzylidene ring have been shown to give mixtures of regioisomeric products (19) because, although the ring opening is always trans-diaxial, systems with conformational movility can react through different interconvertible conformers. p. p. ; ACS Symposium Series; American Chemical Society: Washington, DC, 1992.

Semicyclic Dienes with One or Two Allylic Stereogenic Centers. The semicyclic dienes studied by Fraser-Reid 38 and Giuliano 39 (see Figure 14) bear just one single allylic stereogenic center at position 1 (diene numbering) and the addition took place from the face opposite the allylic alkoxy group. ; ACS Symposium Series; American Chemical Society: Washington, DC, 1992. 3. LOPEZ & LUKACS Pyranose-Derived Dienes and Conjugated Enals 45 same orientation so that reinforcement in the and stereodirecting effect could be predicted Semicyclic Dienes with One Allylic Stereogenic Substituent at Position 2 in the Diene Moiety.

Chem. 1968, 33, 1823. V. J. Org. Chem. 1983, 48, 3269. ; Rokach, J. J. Am. Chem. W. J. Am. Chem. Soc. 1989, 111, 7668. ; Helv. Chim. Acta 1989, 72, 1649. B. Tetrahedron Lett. 1989 ,30, 4921. J. J. Chem. Soc. Perkin Trans. 1 1989, 739. J. J. Chem. Soc. Perkin Trans. 1 1990, 3113. G. J. Am. Chem. Soc. 1986, 108, 7373. ; Thieffry Tetrahedron1978,34,299. ; Lubineau, A. J. Chem. Soc. Perkin Trans. 1 1979, 1795. ; Lloyd-Williams, P. J. Chem. Soc. Chem. Commun. 1987, 423. ; ACS Symposium Series; American Chemical Society: Washington, DC, 1992.

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