A Flexible Asymmetric Synthesis of anti??1, 2??Sulfanyl Amines

D Enders, A Moll, A Schaadt, G Raabe…

Index: Enders, Dieter; Moll, Alexander; Schaadt, Annette; Raabe, Gerhard; Runsink, Jan European Journal of Organic Chemistry, 2003 , # 20 p. 3923 - 3938

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Citation Number: 18

Abstract

Abstract An efficient and flexible asymmetric synthesis of various protected anti-1, 2-sulfanyl amines bearing two adjacent stereogenic centres is described. Key steps are the diastereoselective α-alkylation of α-sulfanylated acetaldehyde-SAMP-hydrazones with various electrophiles and subsequent nucleophilic 1, 2-addition of organocerium reagents to the hydrazone CN double bond. The resulting hydrazines were converted into the title ...