Formal Asymmetric Cycloaddition of Activated α,β-Unsaturated Ketones with α‑Diazomethylphosphonate Mediated by a Chiral Silver SPINOL Phosphate Catalyst
An efficient method for preparing highly functionalized chiral nonspiro-phosphonylpyrazolines via an asymmetric formal 1,3-dipolar cycloaddition reaction of α-diazomethylphosphonate with activated, acyclic α,β-unsaturated ketones, bearing an additional nitrile electron-withdrawing group, has been...
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| Veröffentlicht in: | Organic letters 2019-02, Vol.21 (3), p.593-597 |
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| container_title | Organic letters |
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| creator | Zheng, Bo Chen, Haohua Zhu, Lei Hou, Xiqiang Wang, Yan Lan, Yu Peng, Yungui |
| description | An efficient method for preparing highly functionalized chiral nonspiro-phosphonylpyrazolines via an asymmetric formal 1,3-dipolar cycloaddition reaction of α-diazomethylphosphonate with activated, acyclic α,β-unsaturated ketones, bearing an additional nitrile electron-withdrawing group, has been developed, utilizing an in situ generated chiral silver phosphate catalyst, affording excellent stereoselectivities (up to 98% ee, 99:1 dr) and yields (up to 95%). A stepwise mechanism is proposed based upon density functional M11 calculations. |
| doi_str_mv | 10.1021/acs.orglett.8b03436 |
| format | Article |
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| title | Formal Asymmetric Cycloaddition of Activated α,β-Unsaturated Ketones with α‑Diazomethylphosphonate Mediated by a Chiral Silver SPINOL Phosphate Catalyst |
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