Diastereo- and Enantioselective Synthesis of α-(β-Aminoalkyl)-Substituted γ-Lactams by Michael Addition to Nitroalkenes

Dieter Enders; Pascal Teschner; Gerhard Raabe

doi:10.1055/s-2000-6601

Synlett 2000; 2000(5): 0637-0640
DOI: 10.1055/s-2000-6601

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Diastereo- and Enantioselective Synthesis of α-(β-Aminoalkyl)-Substituted γ-Lactams by Michael Addition to Nitroalkenes

Dieter Enders^* , Pascal Teschner, Gerhard Raabe

^*Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, 52074 Aachen, Germany; Fax + 49(241)8888-127; E-mail: enders@rwth.aachen.de

Abstract

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α-(β-Aminoalkyl)-substituted γ-lactams 5a-e were synthesized in three steps in good overall yields (37-61%) and diastereo- and enantiomeric excesses (de ≥ 96%, ee = 82-≥ 96%). In the key step metalated N-dialkylamino lactam (S)-1 underwent 1,4-addition to nitroalkenes 2 to afford the Michael adducts 3, which were converted to the protected amines 4. After subsequent reductive cleavage of the N-N-bond with lithium in liquid ammonia the title compounds 5 were obtained. The relative and absolute configuration of the major diastereomer was determined by X-ray structure analysis on (R,R,S′)-3b.

asymmetric synthesis - lactams - Michael addition - nitroalkenes - reduction

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