Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 347, Issue 11-13, Pages 1643-1648Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200505148
Keywords
bifunctional organocatalyst; guanidines; nitroaldol; organic catalysis; thioureas
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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).
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