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CN106008328A 含全碳季碳手性中心和氮芳香杂环的α,α-双取代-β-硝基酯类化合物及其衍生物的制备 有权

含全碳季碳手性中心和氮芳香杂环的α,α-双取代-β-硝基酯类化合物及其衍生物的制备
Abstract:
本发明公开了属于有机合成技术领域的一种含全碳季碳手性中心和氮芳香杂环的α,α‑双取代‑β‑硝基酯类化合物及其衍生物的制备。有机溶剂中，在双噁唑啉手性配体‑镍催化剂或膦‑噁唑啉手性配体‑铜催化剂的催化下，2‑乙酰基氮杂芳香烃与α‑取代‑β‑硝基丙烯酸酯反应，合成式I所示含化合物；该化合物进一步转化为式II(1)所示γ‑丁内酯类化合物、式II(2)所示β2,2‑氨基酸酯类化合物、式II(3)所示琥珀酸酯类化合物或式II(4)所示γ‑内酰胺类化合物。所述制备反应条件温和，产率高，光学纯度高，为不对称合成含全碳季碳手性中心和含氮芳香杂环α,α‑双取代‑β‑硝基酯类化合物及其衍生物的提供了工具。
Abstract(English):

The invention discloses preparation of an alpha,alpha-disubstituted-beta-nitro ester compound containing a full-carbon quaternary carbon chiral center and a nitrogen aromatic heterocyclic ring and derivatives thereof. In an organic solvent, under catalysis of a bisoxazoline chiral ligand-nickel catalyst or a phosphine-oxazoline chiral ligand-copper catalyst, 2-acetyl aza aromatic hydrocarbon and alpha-substituted-beta-nitro acrylate are subjected to a reaction to synthesize a compound represented by the formula I; the compound is further converted to gamma-butyrolactone compound represented by the formula II (1), beta 2,2-amino acid ester compound represented by the formula II (2), a succinate compound represented by the formula II (3), or a gamma-lactam compound represented by the formula II (4). The preparation has the advantages of mild reaction conditions, high yield, and high optical purity, and provides a tool for asymmetric synthesis of the alpha,alpha-disubstituted-beta-nitro ester compound containing the full-carbon quaternary carbon chiral center and the nitrogen aromatic heterocyclic ring and the derivatives thereof.

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