Rate enhancement of phase transfer catalyzed conjugate additions by CsCI

Organic Letters

Volumn 11, Issue 9, 2009, Pages 2023-2025

  Kano, Taichi ^a   Kumano, Takeshi ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 66149139305     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900476e     Document Type: Article

References (28)

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4. (d) Shioiri, T.; Ando, A.; Masui, M.; Miura, T.; Tatematsu, T.; Bohsako, A.; Higashiyama, M.; Asakura, C. In Phase-Transfer Catalysis; Halpern, M. E., Ed.; ACS Symposium Series 659; American Chemical Society: Washington, DC, 1997; Chapter 11.
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9. 3 resulted in no product formation. See Supporting Informationfor details.
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20. Use of ether, which is a common solvent for the phase transfer catalyzed conjugate addition reaction, resulted in a moderate yield of 2a (56%) even in the presence of CsCl.
21. Previously, we have reported that addition of achiral phase transfer catalysts involving crown ethers and quaternary ammonium salts drastically accelerated the asymmetric alkylation reaction under phase transfer conditions without affecting the enantioselectivity. See: Shirakawa, S.; Yamamoto, K.; Kitamura, M.; Ooi, T.; Maruoka, K. Angew. Chem., Int. Ed. 2005, 44, 625.
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