Asymmetric Synthesis of Spirocyclic Oxindole δ‑Lactams via NHC-Catalyzed Formal [2+4] Annulation of Aliphatic Aldehydes with Oxindole-Derived α,β-Unsaturated Ketimines
An N-heterocyclic carbene (NHC)-catalyzed formal [2+4] annulation reaction of aliphatic aldehydes with oxindole-derived α,β-unsaturated ketimines under oxidative conditions is reported, affording spirocyclic oxindole δ-lactams with good yields, moderate diastereoselectivies, and good to excellent en...
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| Veröffentlicht in: | Journal of organic chemistry 2019-09, Vol.84 (18), p.12177-12186 |
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| container_end_page | 12186 |
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| container_issue | 18 |
| container_start_page | 12177 |
| container_title | Journal of organic chemistry |
| container_volume | 84 |
| creator | He, Chonglong Li, Zhanhuan Xu, Jianfeng Ren, Hongjun |
| description | An N-heterocyclic carbene (NHC)-catalyzed formal [2+4] annulation reaction of aliphatic aldehydes with oxindole-derived α,β-unsaturated ketimines under oxidative conditions is reported, affording spirocyclic oxindole δ-lactams with good yields, moderate diastereoselectivies, and good to excellent enantioselectivies. This reaction can be readily carried out on a gram scale, and the products could be further transformed to other synthetically useful compounds. |
| doi_str_mv | 10.1021/acs.joc.9b01760 |
| format | Article |
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| source | ACS Publications |
| title | Asymmetric Synthesis of Spirocyclic Oxindole δ‑Lactams via NHC-Catalyzed Formal [2+4] Annulation of Aliphatic Aldehydes with Oxindole-Derived α,β-Unsaturated Ketimines |
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