KUBÁŇ, Juraj, Alex KOLAROVIČ, Ĺubor FIŠERA, Volker JÄGER, Otakar HUMPA, Naďa PRONAYOVÁ and P ERTL. Stereoselectivity of 1,3-dipolar cycloadditions of D-erythrose and D-threose derived nitrones with methyl acrylate. Synlett. 2001, No 12, p. 1862-1865. ISSN 0936-5214.
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Basic information
Original name Stereoselectivity of 1,3-dipolar cycloadditions of D-erythrose and D-threose derived nitrones with methyl acrylate
Name (in English) Stereoselectivity of 1,3-dipolar cycloadditions of D-erythrose and D-threose derived nitrones with methyl acrylate
Authors KUBÁŇ, Juraj, Alex KOLAROVIČ, Ĺubor FIŠERA, Volker JÄGER, Otakar HUMPA, Naďa PRONAYOVÁ and P ERTL.
Edition Synlett, 2001, 0936-5214.
Other information
Type of outcome Article in a journal
Confidentiality degree is not subject to a state or trade secret
Impact factor Impact factor: 2.465
Organization unit Central European Institute of Technology
UT WoS 000172596400010
Keywords in English cycloadditions; nitrones; isoxazolidines; stereoselectivity; heterocycles
Tags cycloadditions, heterocycles, isoxazolidines, nitrones, stereoselectivity
Changed by Changed by: RNDr. Otakar Humpa, učo 745. Changed: 28/2/2003 14:29.
Abstract (in English)
1,3-Dipolar cycloadditions between the D-erythrose and D-threose derived nitrones and methyl acrylate proceed in a regiospecific manner to afford the corresponding 3,5-disubstituted diastereomeric isoxazolidines in good yields. The stereoselectivity was dependent on the steric hindrance of the nitrone. The major products were found to have the C-3/C-4' erythro and C-3/C-5 cis relative configuration. Its formation can be rationalized by less hindered endo attack of the Z-nitrone in an antiperiplanar manner with respect to the largest group of the cyclic acetal.
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