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À propos de : Synthesis of Highly Substituted Enantiopure Piperazines andKetopiperazines from Vicinal N-Sulfinyl Diamines        

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  • Synthesis of Highly Substituted Enantiopure Piperazines andKetopiperazines from Vicinal N-Sulfinyl Diamines
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  • Enantiopure 1-benzyl-2,3-disubstituted piperazines (4) have been synthesized by treatment of N-sulfinyl-N-benzyldiamino alcohols (1) with diethyl oxalate and sodium methoxide followed by reduction withborane. Alternatively, the sulfinamido group was preserved by an N-acylation/cyclization protocol usingα-chloroacetyl chloride that led to the synthesis of N-sulfinyl ketopiperazines (11). Ensuing eliminationof the sulfinyl group with NaH produced imino ketopiperazines (9) that are suitably functionalized fornucleophilic addition to the imino moiety. Stereoselective and high yielding allylation of iminoketopiperazines (9c) was achieved under Barbier conditions using CeCl3·7H2O as the additive.
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