Stereoselectivity of 1,3-dipolar cycloadditions of D-erythrose and D-threose derived nitrones with methyl acrylate

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.

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

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Other information

Type of outcome

Článek v odborném periodiku

Confidentiality degree

není předmětem státního či obchodního tajemství

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

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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.