Regio-and Enantioselective Substitution of Primary Endocyclic Allylic Sulfoximines with Organocopper and Organocuprate Reagents. The Importance of Iodide for the …

…, J Bund, M Scommoda, J Brandt, G Raabe

Index: Gais, Hans-Joachim; Mueller, Harald; Bund, Joerg; Scommoda, Matthias; Brandt, Jochen; Raabe, Gerhard Journal of the American Chemical Society, 1995 , vol. 117, # 9 p. 2453 - 2466

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Citation Number: 65

Abstract

Abstract: The endocyclic N-substituted allylic sulfoximines 17-20 and 26 were synthesized from the corresponding cycloalkanones and the various (8-S-(lithiomethyl)-S- phenylsulfoximines in enantiomerically pure form in yields of 60-70% in a process involving the isomerization of the intermediate vinylic sulfoximines. Desilylation of 26 gave the parent NH sulfoximine 27 from which the N-sulfonylsulfoximines 28 and 29 were prepared. The X ...