TY - JOUR
T1 - The effectiveness of proteinogenic amino acids in the asymmetric aldol reaction in DMSO and aqueous DMSO
AU - Hayashi, Yujiro
AU - Itoh, Takahiko
AU - Nagae, Norio
AU - Ohkubo, Masahiro
AU - Ishikawa, Hayato
PY - 2008/6/13
Y1 - 2008/6/13
N2 - The effects of twenty proteinogenic amino acids have been investigated in the aldol reaction of aldehyde and ketone in DMSO and aqueous DMSO (in the presence of three equivalents of water). Not only proline but also other amino acids promote the al-dol reaction enantioselectively. The effect of water varies with amino acid, and water does not affect the enantioselectivity in most cases, the exceptions being Pro, Ser and His. In the case of Pro, large positive effects on diastereo- and enantioselectivities were ob-served in the reaction of a-substituted methyl ketone, while no ef-fect was observed in that of methyl ketone.
AB - The effects of twenty proteinogenic amino acids have been investigated in the aldol reaction of aldehyde and ketone in DMSO and aqueous DMSO (in the presence of three equivalents of water). Not only proline but also other amino acids promote the al-dol reaction enantioselectively. The effect of water varies with amino acid, and water does not affect the enantioselectivity in most cases, the exceptions being Pro, Ser and His. In the case of Pro, large positive effects on diastereo- and enantioselectivities were ob-served in the reaction of a-substituted methyl ketone, while no ef-fect was observed in that of methyl ketone.
KW - asymmetric synthesis, aldol reactions, organocatalyst, amino acids, water
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U2 - 10.1055/s-2008-1077789
DO - 10.1055/s-2008-1077789
M3 - Article
AN - SCOPUS:46649117893
SN - 0936-5214
SP - 1565
EP - 1570
JO - Synlett
JF - Synlett
IS - 10
ER -