TY - JOUR
T1 - Highly enantioselective asymmetric autocatalysis induced by chiral ionic crystals of sodium chlorate and sodium bromate
AU - Sato, Itaru
AU - Kadowaki, Kousuke
AU - Ohgo, Yasushi
AU - Soai, Kenso
N1 - Funding Information:
Financial support from the Ministry of Education, Culture, Sports, Science and Technology (MEXT), the New Energy and Industrial Technology Development Organization (NEDO) is gratefully acknowledged. We thank Prof. Naoyuki Koide and Dr. Takashi Mihara of Department of Chemistry of our university for a microscope measurement of the size of the powder of sodium chlorate.
PY - 2004/7/12
Y1 - 2004/7/12
N2 - Chiral crystals of sodium chlorate and sodium bromate induced highly enantioselective organic synthesis in combination with asymmetric autocatalysis. (S)-5-Pyrimidyl alkanols with up to 98% ee were obtained in the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehydes in the presence of d-sodium chlorate. On the other hand, (R)-5-pyrimidyl alkanols with up to 98% ee were obtained for the corresponding reaction in the presence of l-sodium chlorate. Chiral crystals of d- and l-sodium bromate were also found to work as chiral initiators.
AB - Chiral crystals of sodium chlorate and sodium bromate induced highly enantioselective organic synthesis in combination with asymmetric autocatalysis. (S)-5-Pyrimidyl alkanols with up to 98% ee were obtained in the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehydes in the presence of d-sodium chlorate. On the other hand, (R)-5-pyrimidyl alkanols with up to 98% ee were obtained for the corresponding reaction in the presence of l-sodium chlorate. Chiral crystals of d- and l-sodium bromate were also found to work as chiral initiators.
KW - Asymmetric autocatalysis
KW - Asymmetric synthesis
KW - Crystals
KW - Enantiomorphism
KW - Surface
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U2 - 10.1016/j.molcata.2004.03.010
DO - 10.1016/j.molcata.2004.03.010
M3 - Article
AN - SCOPUS:2542466797
SN - 1381-1169
VL - 216
SP - 209
EP - 214
JO - Journal of Molecular Catalysis A: Chemical
JF - Journal of Molecular Catalysis A: Chemical
IS - 2
ER -