Tetrahedron

Organolithium-induced synthesis of acyclic unsaturated amino alcohols from epoxides of dihydropyrroles and tetrahydropyridines

DM Hodgson, TJ Miles, J Witherington

Index: Hodgson, David M.; Miles, Timothy J.; Witherington, Jason Tetrahedron, 2003 , vol. 59, # 49 p. 9729 - 9742

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Citation Number: 19

Abstract

The alkylative double ring-opening of Bus-protected 2, 5-dihydropyrrole epoxides 13 and 29 with organolithiums to give 3-substituted 1-aminobut-3-en-2-ols 13–19 and 30–32 are described. Bus-protected tetrahydropyridine epoxide 38 reacts with organolithiums to give 4- substituted 1-aminobut-4-en-3-ols 39 and tetrahydropyridinol 40.