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

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Authors

MELŠA Petr MAZAL Ctibor

Year of publication 2002
Type Article in Periodical
Magazine / Source Collection of Czechoslovak Chemical Communications
MU Faculty or unit

Faculty of Science

Citation
Web http://cccc.uochb.cas.cz
Field Organic chemistry
Keywords 1;3-dipolar cycloadditions; methylene lactones; stereoselective synthesis; spiro compounds; ortho esters
Description 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.
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