| Autor: |
Yanxiong Ke, Chuncheng Zou, Jinxing Ye, Yanting Lv, Lei Zhang, Gonghua Song, Min Lu, Lei Yang, Zhen Liu, Xin Li |
| Rok vydání: |
2021 |
| Předmět: |
|
| Zdroj: |
Organic Chemistry Frontiers. 8:4758-4766 |
| ISSN: |
2052-4129 |
| Popis: |
Regioselective and diastereodivergent asymmetric vinylogous Michael addition (AVMA) between β-substituted-cyclohexenones and nitroalkenes via dienamine activation under complementary chiral aminocatalysts was reported. γ-Regioselective AVMA of β-alkyl-cyclohex-2-enones via a linear exo-dienamine mechanism and γ′-regioselective functionalization of β-substituted-cyclohex-3-enones via a cyclic extended endo-dienamine mechanism were reported in satisfactory yields with high enantio- and diastereoselectivities. DFT calculations reasonably explained that the diastereoselectivity of the reactions at the γ- and γ′-positions is achieved by regulating the orientation of the nitroalkenes through the hydrogen-bonding interaction and steric hindrance effect. Furthermore, the four different configurations of the γ- and γ′-adducts were diversified to the corresponding enantioenriched spirocyclic ketones and cis-2-decalones with multiple chiral centers. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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