Chemistry Letters

Asymmetric Syntheses of Pharmaceuticals Containing a Cyclopropane Moiety Using Catalytic Asymmetric Simmons–Smith Reactions of Allylalcohols: Syntheses of …

…, T Noguchi, M Kawasaki, M Kishida, T Nagai, N Imai…

Index: Ishizuka, Yuki; Fujimori, Hirohisa; Noguchi, Takuya; Kawasaki, Masashi; Kishida, Mari; Nagai, Takuya; Imai, Nobuyuki; Kirihara, Masayuki Chemistry Letters, 2013 , vol. 42, # 10 p. 1311 - 1313

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Citation Number: 5

Abstract

Asymmetric synthesis of tranylcypromine was achieved using an enantioselective Simmons– Smith cyclopropanation catalyzed by a simple disulfonamide derived from an α-amino acid. The optically active milnacipran was also synthesized by porcine pancreas lipase-catalyzed selective monoacylation of the C4-hydroxy group in (Z)-2-phenylbut-2-ene-1, 4-diol and the enantioselective Simmons–Smith cyclopropanation as the key steps.