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. Collection of Czechoslovak Chemical Communications. Prague: Inst. Org. Chem. Biochem. Acad. Sci. CR, vol. 67, No 3, p. 353-364. ISSN 0010-0765. 2002.
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Basic information
Original name 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
Authors MELŠA, Petr (203 Czech Republic) and Ctibor MAZAL (203 Czech Republic, guarantor).
Edition Collection of Czechoslovak Chemical Communications, Prague, Inst. Org. Chem. Biochem. Acad. Sci. CR, 2002, 0010-0765.
Other information
Original language English
Type of outcome Article in a journal
Field of Study 10401 Organic chemistry
Country of publisher Czech Republic
Confidentiality degree is not subject to a state or trade secret
WWW URL
Impact factor Impact factor: 0.848
RIV identification code RIV/00216224:14310/02:00006105
Organization unit Faculty of Science
Keywords in English 1;3-dipolar cycloadditions; methylene lactones; stereoselective synthesis; spiro compounds; ortho esters
Tags 1, 3-dipolar cycloadditions, methylene lactones, ortho esters, spiro compounds, stereoselective synthesis
Changed by Changed by: doc. RNDr. Ctibor Mazal, CSc., učo 22. Changed: 20/5/2003 15:48.
Abstract
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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MSM 143100011, plan (intention)Name: Struktura a vazebné poměry, vlastnosti a analýza syntetických a přírodních molekulových ansamblů
Investor: Ministry of Education, Youth and Sports of the CR, Structure and character of bonding, properties and analysis of synthetic and natural molecular ensembles
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