Tetrahedron: Asymmetry

Two aspects of the desymmetrization of selected prochiral aromatic or vinylic dihalides: enantioselective halogen–lithium exchange and prochiral recognition in chiral …

CA Fan, B Ferber, HB Kagan, O Lafon, P Lesot

Index: Fan, Chun-An; Ferber, Benoit; Kagan, Henri B.; Lafon, Olivier; Lesot, Philippe Tetrahedron Asymmetry, 2008 , vol. 19, # 23 p. 2666 - 2677

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Citation Number: 21

Abstract

Several classes of prochiral dihalides have been identified as potential candidates for asymmetric halogen–lithium exchange. Bis-aryl compounds 1 and 2, 2, 3- dibromonorbornadiene 3, and 1, 2-diiodoferrocene 4 were prepared and used as substrates in the asymmetric halogen–lithium exchange reaction. The enantioselective mono-lithiation was achieved in good yields by various combinations of n-BuLi and chiral ligands. ...