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@article{404023, author = {Melša, Petr and Mazal, Ctibor}, article_location = {Prague}, article_number = {3}, keywords = {1;3-dipolar cycloadditions; methylene lactones; stereoselective synthesis; spiro compounds; ortho esters}, language = {eng}, issn = {0010-0765}, journal = {Collection of Czechoslovak Chemical Communications}, title = {pi-Facial selectivity in 1,3-dipolar cycloaddition reactions of alpha-methylidene-gamma-lactone substituted by 4-methyl-2,6,7-trioxabicyclo[2.2.2]octanyl group in gamma-position}, url = {cccc.uochb.cas.cz}, volume = {67}, year = {2002} }
TY - JOUR ID - 404023 AU - Melša, Petr - Mazal, Ctibor PY - 2002 TI - pi-Facial selectivity in 1,3-dipolar cycloaddition reactions of alpha-methylidene-gamma-lactone substituted by 4-methyl-2,6,7-trioxabicyclo[2.2.2]octanyl group in gamma-position JF - Collection of Czechoslovak Chemical Communications VL - 67 IS - 3 SP - 353 EP - 353 PB - Inst. Org. Chem. Biochem. Acad. Sci. CR SN - 00100765 KW - 1;3-dipolar cycloadditions KW - methylene lactones KW - stereoselective synthesis KW - spiro compounds KW - ortho esters UR - cccc.uochb.cas.cz N2 - Diastereoselectivity of 1,3-dipolar cycloaddition reactions of benzyl azide, diazomethane, a nitrile oxide and a nitrile imine to alpha-methylidene-gamma-lactone dipolarophile was effectively controlled by a bulky substituent, 4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl (OBO), in gamma-position of the dipolarophile. The dipoles added from the less hindered face of the double bond with an excellent selectivity. The enantiomerically pure dipolarophile was prepared from the easily available (S)-5-oxotetrahydrohydrofuran-2-carboxylic acid. ER -
MELŠA, Petr and Ctibor MAZAL. pi-Facial selectivity in 1,3-dipolar cycloaddition reactions of alpha-methylidene-gamma-lactone substituted by 4-methyl-2,6,7-trioxabicyclo[2.2.2]octanyl group in gamma-position. \textit{Collection of Czechoslovak Chemical Communications}. Prague: Inst. Org. Chem. Biochem. Acad. Sci. CR, 2002, vol.~67, No~3, p.~353-364. ISSN~0010-0765.
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