Tetrahedron Letters

Intramolecular amidocyclopropanation reactions using diethoxymethyl-functionalised lactams as organozinc carbenoid precursors

L Jerome, TD Sheppard, AE Aliev, WB Motherwell

Index: Jerome, Laure; Sheppard, Tom D.; Aliev, Abil E.; Motherwell, William B. Tetrahedron Letters, 2009 , vol. 50, # 26 p. 3709 - 3712

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Citation Number: 5

Abstract

Intramolecular amidocyclopropanation reactions of diethoxymethyl-lactams containing a pendant alkene were examined using zinc/TMSCl. With a range of 4–6-membered lactams, bicyclic amidocyclopropanes were obtained with very high diastereoselectivity with a preference for the formation of the more hindered endo-cyclopropane.