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- W2776594816 abstract "2,4,6-Trisubstituted piperidines were synthesized via a 5-step sequence in overall moderate to good yield and excellent stereoselectivity. A Michael addition to an α,β-unsaturated ketone by an N-sulfinyl metalloenamine (formed in situ by deprotonation of the corresponding ketimine with LDA followed by transmetallation with ZnBr2) afforded the addition product in good yield and excellent diastereoselectivity. Reduction using L-selectride, followed by DMP oxidation resulted in a syn-5-amino-ketone, while the anti-product was obtained using NaBH4/Ti(OEt)4 as a reductant. After cleavage of the N-tert-butylsulfinyl group using HCl, the aminoketone was readily converted into 2,4,6-trisubstituted piperidine in high diastereoselectivity using DIBAL-H." @default.
- W2776594816 created "2018-01-05" @default.
- W2776594816 date "2005-10-25" @default.
- W2776594816 modified "2023-10-14" @default.
- W2776594816 title "Asymmetric Synthesis of Piperidine via N-Sulfinyl Ketimines" @default.
- W2776594816 doi "https://doi.org/10.1055/s-2005-916079" @default.
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