Diastereoselective synthesis of 2, 3-disubstituted tetrahydrofuran synthons via the iodoetherification reaction. A transition state model based rationalization of the …

M Labelle, Y Guindon

Index: Labelle, Marc; Guindon, Y. Journal of the American Chemical Society, 1989 , vol. 111, # 6 p. 2204 - 2210

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Citation Number: 68

Abstract

Abstract: The kinetically controlled iodoetherification reaction of ethyl (S, E)-4, 6-dihydroxy-2- hexenoate (1) gives the synthetically useful synthon 2, in which two new stereogenic centers have been generated, with selectivities up to 11: l. The mechanism of this allylic asymmetry transfer was probed by changing the allylic stereogenic substituent, and the order of efficacy for asymmetric induction was found to be F> OH 1. OMe> Me. This result ruled out several ...