Homoallylic chiral induction in the synthesis of 2, 4-disubstituted tetrahydrofurans by iodoetherification. Synthetic scope and chiral induction mechanism

…, HE Morton, Y Guindon, JP Springer

Index: Labelle, M.; Morton, H. E.; Guindon, Y.; Springer, J. P. Journal of the American Chemical Society, 1988 ,  vol. 110,  # 14  p. 4533 - 4540

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Citation Number: 54

Abstract

Abstract: Chiral induction generating two new stereogenic centers has been observed in the iodoetherification of optically active ethyl 5.6-dihydroxyhexenoate. Of the four possible isomeric tetrahydrofuran products, only two were obtained in ratios up to 12: l favoring the trans orientation of the tetrahydrofuran substituents. The olefin geometry was found to control the chirality at the exocyclic iodide-bearing carbon. Inversion of the original ...