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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 a 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, roč.~67, č.~3, s.~353-364. ISSN~0010-0765.
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