Guanidine-thiourea bifunctional organocatalyst for the asymmetric Henry (nitroaldol) reaction

Guanidine-thiourea bifunctional organocatalyst for the asymmetric Henry (nitroaldol) reaction
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DOI:
10.1002/adsc.200505148
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发表时间:
2005-10-01
影响因子:
5.4
通讯作者:
Nagasawa, K
Nagasawa, K
中科院分区:
化学2区
文献类型:
--
作者:
Sohtome, Y;Hashimoto, Y;Nagasawa, K

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研制了具有胍基和硫脲官能团的新型双功能催化剂,用于不对称亨利(硝基)反应。催化剂的各种结构发展表明,该化合物具有十八烷基取代胍和硫脲基团,并与苯丙氨酸衍生的手性间隔物(即1e)相连,有效地促进了亨利反应。这种双功能有机催化剂也具有高不对称诱导C,具有脂肪族环醛和支链脂肪族醛(82-90% ee)。
Novel bifunctional catalysts having guanidine and thiourea functional groups were developed for the asymmetric Henry (nitroaldol) reaction. Various structural developments of the catalyst revealed that the compound having an octadecyl-substituted guanidine and thiourea groups linked with a chiral spacer derived from phenylalanine, i.e., 1e, efficiently promoted the Henry reaction. This bifunctional organocatalyst le also gave high asymmetric inductions C, with aliphatic cyclic aldehydes and branched aliphatic aldehydes (82-90% ee).