1,3-Dipolar cycloaddition of nitrone 7 to ,-unsaturated -lactones: non-chiral 2, racemic mixture 3/3ent, D-glycero 3 and D-threo 15 proceeds with high stereoselectivity in the case of 2 and 15, and with a significant kinetic resolution in the case of the racemate 3/3ent. The endo approach of reactants was not observed. CD-spectroscopy proved an attractive tool for determination of the absolute configuration of cycloadducts.
1,3-Dipolar Cycloaddition of a Nitrone Derived from (S)-Malic Acid to α,β-Unsaturated δ-Lactones / D. Socha; M. Jurczak; J. Frelek; A. Klimek; J. Rabiczko; Z. Urbanczyk-Lipkowska; K. Suwinska; M. Chmielewski; F. Cardona; A. Goti; A. Brandi. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - STAMPA. - 12:(2001), pp. 3163-3172.
1,3-Dipolar Cycloaddition of a Nitrone Derived from (S)-Malic Acid to α,β-Unsaturated δ-Lactones
CARDONA, FRANCESCA;GOTI, ANDREA;BRANDI, ALBERTO
2001
Abstract
1,3-Dipolar cycloaddition of nitrone 7 to ,-unsaturated -lactones: non-chiral 2, racemic mixture 3/3ent, D-glycero 3 and D-threo 15 proceeds with high stereoselectivity in the case of 2 and 15, and with a significant kinetic resolution in the case of the racemate 3/3ent. The endo approach of reactants was not observed. CD-spectroscopy proved an attractive tool for determination of the absolute configuration of cycloadducts.
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