Tetrahedron letters

Imidoyllithiums: Masked acyllithium reagents

E Alonso, DJ Ramón, M Yus

Index: Alonso, Emma; Ramon, Diego J.; Miguel, Yus Tetrahedron Letters, 1997 , vol. 38, # 51 p. 8903 - 8906

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Citation Number: 13

Abstract

The reaction of chloroimines 1 with an excess of lithium powder and a catalytic amount of naphthalene (4 mol%) in THF at− 78° C leads to the corresponding imidoyllithium intermediates 2, which by treatment with different electrophiles [PriCHO, ButCHO, n- C5H11CHO, PhCHO, Et2CO,(CH2) 5CO, EtOCOCl, MeOCSCl, n-C7H15CON (Me) OMe] at− 78 to 20° C and final hydrolysis with water affords functionalysed imines 3. For starting ...