期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 354, 期 18, 页码 3523-3532出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201200658
关键词
asymmetric catalysis; C?C bond formation; Michael addition; organic catalysis; strained molecules
资金
- French Ministry of Research
- ANR [ANR-07-BLAN-0269, ANR-07-CP2D-06]
- Aix-Marseille Universite
- CNRS
- Agence Nationale de la Recherche (ANR) [ANR-07-BLAN-0269] Funding Source: Agence Nationale de la Recherche (ANR)
Synthetic applications of cyclobutanones other than ring expansion and fragmentation reactions are rare. Herein, highly efficient diastereo- and enantioselective organocatalytic Michael additions of 2-substituted cyclobutanone derivatives to nitroalkenes are reported allowing the stereocontrolled creation of all-carbon quaternary centers. The approach relies on both the use of Bronsted base/hydrogen-bond donor bifunctional organocatalysts, and importantly, the specific stabilization and activation of cyclobutanone with a secondary amide moiety. The reaction was found to nicely accommodate a broad scope of substrates, allowing the control of up to three contiguous stereogenic centers. This work has opened new synthetic opportunities.
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