Highly diastereoselective synthesis of 1,2-epoxy-4-hydroxyalkyl carbamates. Masked and activated α,γ-dihydroxy-alkanals and -alkanones

Dieter Hoppe; Jörg Lüßmann; Peter G. Jones; Dieter Schmidt; In Memory: G.M. Sheldrick (1942–2025)

doi:10.1016/s0040-4039(00)84857-1

Highly diastereoselective synthesis of 1,2-epoxy-4-hydroxyalkyl carbamates. Masked and activated α,γ-dihydroxy-alkanals and -alkanones

Tetrahedron Letters 27(31): 3591-3594

Article 1986 English

Abstract

1 min read

( Z )- anti -4-Hydroxy-1-alkenylcarbamates 1 yield, with essentially complete diastereoselectivity, the epoxides 2 with (1 Z -2-3- anti -3,4- anti -configuration on treatment with tert -butylhydroperoxide/vanadylbis(acetoacetonate).

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Highly diastereoselective synthesis of 1,2-epoxy-4-hydroxyalkyl carbamates. Masked and activated α,γ-dihydroxy-alkanals and -alkanones

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