Simple chiral crown ethers complexed with potassium tert-butoxide as efficient catalysts for asymmetric Michael additions

作者: Shin Aoki , Shigeki Sasaki , Kenji Koga

DOI: 10.1016/S0040-4039(01)93942-5

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摘要: Abstract Simple C2-symmetric chiral crown ether 1 complexed with KOtBu was found to work as an efficient catalyst in Michael additions cause high asymmetric induction. The results various ethers catalysts suggest that diaxial-like conformation of the vicinal methyl groups 1·potassium enolate complex is responsible for

参考文章(9)
Scott T. Joll, Jerald S. Bradshaw, Reed M. Izatt, Synthetic chiral macrocyclic crown ligands: A short review Journal of Heterocyclic Chemistry. ,vol. 19, pp. 3- 19 ,(1982) , 10.1002/JHET.5570190101
Manuel Alonso-Lopez, Jesus Jimenez-Barbero, Manuel Martin-Lomas, Soledad Penades, Synthesis, complexing properties and applications in asymmetric synthesis of bis-lacto-18-crown-6 compounds Tetrahedron. ,vol. 44, pp. 1535- 1543 ,(1988) , 10.1016/S0040-4020(01)85932-9
Mayumi Takasu, Hiroaki Wakabayashi, Kyoji Furuta, Hisashi Yamamoto, Conjugate additions of the crown-potassium enolate complexes Tetrahedron Letters. ,vol. 29, pp. 6943- 6946 ,(1988) , 10.1016/S0040-4039(00)88481-6
Manuel Alonso-López, Manuel Martin-Lomas, Soledad Penadés, Asymmetric Michael reaction using macrocyclic lactose derivatives as chiral catalysts. Tetrahedron Letters. ,vol. 27, pp. 3551- 3554 ,(1986) , 10.1016/S0040-4039(00)84847-9
J FRASER STODDART, None, The extramolecular chemical approach to enzyme analogues Biochemical Society Transactions. ,vol. 15, pp. 1188- 1191 ,(1987) , 10.1042/BST0151188
Donald J. Cram, Dotsevi Y. Sogah, Chiral complexes polymerize methacrylate esters to give helical polymers that mutarotate by uncoiling Journal of the American Chemical Society. ,vol. 107, pp. 8301- 8302 ,(1985) , 10.1021/JA00312A103
Donald J. Cram, G. D. Y. Sogah, Chiral crown complexes catalyse Michael addition reactions to give adducts in high optical yields Journal of the Chemical Society, Chemical Communications. pp. 625- 628 ,(1981) , 10.1039/C39810000625
J. Fraser Stoddart, Chiral Crown Ethers Topics in Stereochemistry. ,vol. 17, pp. 207- 288 ,(2007) , 10.1002/9780470147269.CH3
Eckehard V. Dehmlow, Christiane Sauerbier, Enantioselektive Phasentransfer-Katalyse durch optisch aktive Kronenether Liebigs Annalen der Chemie. ,vol. 1989, pp. 181- 185 ,(1989) , 10.1002/JLAC.198919890135