Influence of the Bridgehead Substituent on the Stereoselective Leuckart Reaction of 2??Norbornanones− Skeletal Rearrangement versus Structural Retention

…, A García Fraile, P Martínez??Ruiz

Index: Martinez, Antonio Garcia; Vilar, Enrique Teso; Fraile, Amelia Garcia; Martinez-Ruiz, Paloma European Journal of Organic Chemistry, 2001 , # 15 p. 2805 - 2808

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Citation Number: 9

Abstract

Abstract The synthesis of chiral amine norbornane derivatives has been achieved by means of the Leuckart reaction of various 2-norbornanones. We propose an ionic mechanism for this process in which the formation of a 2-formylamino-2-norbornyl cation is the common initial step. The reaction pathway and the isolated products are strongly dependent on the nature of the bridgehead substituents; hydrogen and alkyl groups yield only enantiopure 2 ...