The 1,3-dipolar cycloadditions of pyrroline N-oxide (1) with (1R,2S)-trans-2-phenylcyclohexyl- and with (1R,2S,5R)-8- phenylmenthyl-pent-2-enoates (9 and 10) proceed with opposite diastereoselectivities. The two enantiomers of a new dihydroxyindolizidine, (+)-6 and (-)-6, were synthesized using 4 and 5, respectively, as the chiral auxiliary.
Enantioselective Synthesis of (7R,8R,8aR) and (7S,8S,8aS)-7-Hydroxy-8-indolizidin-methanol by 1,3-Dipolar Cycloaddition of 1-Pyrroline-N-Oxide to Chiral Pentenoates / F. M. Cordero; C. Faggi; F. De Sarlo; A. Brandi. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 2000:(2000), pp. 3595-3600.
Enantioselective Synthesis of (7R,8R,8aR) and (7S,8S,8aS)-7-Hydroxy-8-indolizidin-methanol by 1,3-Dipolar Cycloaddition of 1-Pyrroline-N-Oxide to Chiral Pentenoates
CORDERO, FRANCA MARIA;FAGGI, CRISTINA;DE SARLO, FRANCESCO;BRANDI, ALBERTO
2000
Abstract
The 1,3-dipolar cycloadditions of pyrroline N-oxide (1) with (1R,2S)-trans-2-phenylcyclohexyl- and with (1R,2S,5R)-8- phenylmenthyl-pent-2-enoates (9 and 10) proceed with opposite diastereoselectivities. The two enantiomers of a new dihydroxyindolizidine, (+)-6 and (-)-6, were synthesized using 4 and 5, respectively, as the chiral auxiliary.
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