TY - JOUR
T1 - 3-Pyrroline-1-carbonyl (Pyroc) group
T2 - A removable protecting group for the kinetic resolution of racemic carboxylic acids and alcohols through catalytic asymmetric acylation
AU - Sakakura, Akira
AU - Umemura, Shuhei
AU - Ishihara, Kazuaki
PY - 2009/6
Y1 - 2009/6
N2 - The O-3-pyrroline-1-carbonyl (O-Pyroc) group and 3-pyrrolinamide are useful removable protecting groups for the kinetic resolution of racemic α-hydroxycarboxylic acids, β-hydroxycarboxylic acids, 1,2-dicarboxylic acids, and 1,2-diols using the L-histidine-derived bifunctional catalysts. The Pyroc group can be easily introduced from Pyroc chloride. Selective deprotection of the Pyroc group and 3-pyrrolinamide can be carried out via DDQ oxidation followed by hydrolysis using sodium hydroxide, without epimerization.
AB - The O-3-pyrroline-1-carbonyl (O-Pyroc) group and 3-pyrrolinamide are useful removable protecting groups for the kinetic resolution of racemic α-hydroxycarboxylic acids, β-hydroxycarboxylic acids, 1,2-dicarboxylic acids, and 1,2-diols using the L-histidine-derived bifunctional catalysts. The Pyroc group can be easily introduced from Pyroc chloride. Selective deprotection of the Pyroc group and 3-pyrrolinamide can be carried out via DDQ oxidation followed by hydrolysis using sodium hydroxide, without epimerization.
KW - 3-pyrroline-1-carbonyl (Pyroc)
KW - Asymmetric acylation
KW - Kinetic resolution
KW - L-histidine framework
KW - Protective and removable
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UR - http://www.scopus.com/inward/citedby.url?scp=67649378855&partnerID=8YFLogxK
U2 - 10.1055/s-0029-1217321
DO - 10.1055/s-0029-1217321
M3 - Article
AN - SCOPUS:67649378855
SN - 0936-5214
SP - 1647
EP - 1650
JO - Synlett
JF - Synlett
IS - 10
ER -