Tetrahedron letters

A highly diastereoselective synthesis of (E)-B-2-(1-cyclopropyl-1-alkenyl)-1, 3, 2-dioxaborinanes. Isolation and oxidation to alkyl cyclopropyl ketones

NG Bhat, L Garcia, V Tamez

Index: Bhat, Narayan G.; Garcia, Laura; Tamez Jr., Victoriano Tetrahedron Letters, 2003 , vol. 44, # 38 p. 7175 - 7177

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Citation Number: 2

Abstract

A convenient, novel synthesis of alkyl cyclopropyl ketones based on Z-1-bromo-1- alkenylboronate esters is developed. α-Bromo-(Z)-1-alkenylboronate esters readily available from literature procedures smoothly undergo a reaction with cyclopropylmagnesium bromide in tetrahydrofuran to provide the corresponding 'ate'complexes. These 'ate'complexes undergo intramolecular nucleophilic substitution ...