Synthesis of Chiral 1, 3??Diamines Derived from cis??2??Benzamidocyclohexanecarboxylic Acid and Their Application in the Cu??Catalyzed Enantioselective Henry …

K Kodama, K Sugawara, T Hirose

Index: Hirose, Takuji; Sugawara, Kazuyuki; Kodama, Koichi Journal of Organic Chemistry, 2011 , vol. 76, # 13 p. 5413 - 5428

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Citation Number: 29

Abstract

Abstract In this study, 13 different chiral 1, 3-diamines were synthesized from (−)-cis-2- benzamidocyclohexanecarboxylic acid. They were successfully applied as ligands in the Cu- catalyzed asymmetric Henry reaction between benzaldehyde and nitromethane. It was confirmed that the enantioselectivity of the product could be controlled by the substituents on the two amino groups. A time-course study revealed a decrease in product ...