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2000 stereochemistry stereochemistry (general, optical resolution) O 0030 10 - 036 Diastereoselective Synthesis of 2-Isoxazolines via Silaketal Tethered 1,3-Dipolar Cycloadditions. — High levels of stereoselectivity are obtained in intramolecular cycloaddition reactions of silaketals substituted at the allylic positions [cf. (I), (IV)], while only moderate stereoselectivity is observed in intramolecular cycloadditions of precursors having only a stereo- center in α-position to the nitrile oxide moiety [cf. (VII), conditions A)]. The stereochemistry is reversed by using silyl nitronates as the dipole [conditions B)]. — (MARRUGO, HERIKA; DOGBEAVOU, ROMAIN; BREAU, LIVAIN; Tetrahedron Lett. 40 (1999) 51, 8979-8983; Dep. Chem., Univ. Quebec, Montreal, Que. H3C 3P8, Can.; EN) 1

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Page 1: ChemInform Abstract: Diastereoselective Synthesis of 2-Isoxazolines via Silaketal Tethered 1,3-Dipolar Cycloadditions

2000 stereochemistry

stereochemistry (general, optical resolution)O 0030

10 - 036Diastereoselective Synthesis of 2-Isoxazolines via Silaketal Tethered1,3-Dipolar Cycloadditions. — High levels of stereoselectivity areobtained in intramolecular cycloaddition reactions of silaketals substituted atthe allylic positions [cf. (I), (IV)], while only moderate stereoselectivity isobserved in intramolecular cycloadditions of precursors having only a stereo-center in α-position to the nitrile oxide moiety [cf. (VII), conditions A)]. Thestereochemistry is reversed by using silyl nitronates as the dipole [conditionsB)]. — (MARRUGO, HERIKA; DOGBEAVOU, ROMAIN; BREAU, LIVAIN;Tetrahedron Lett. 40 (1999) 51, 8979-8983; Dep. Chem., Univ. Quebec,Montreal, Que. H3C 3P8, Can.; EN)

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