Highly enantioselective asymmetric autocatalysis induced by chiral ionic crystals of sodium chlorate and sodium bromate

Itaru Sato; Kousuke Kadowaki; Yasushi Ohgo; Kenso Soai

doi:10.1016/j.molcata.2004.03.010

Highly enantioselective asymmetric autocatalysis induced by chiral ionic crystals of sodium chlorate and sodium bromate

Itaru Sato, Kousuke Kadowaki, Yasushi Ohgo, Kenso Soai

SCI - Research and Analytical Center for Giant Molecules

Research output: Contribution to journal › Article › peer-review

51 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	209-214
Number of pages	6
Journal	Journal of Molecular Catalysis A: Chemical
Volume	216
Issue number	2
DOIs	https://doi.org/10.1016/j.molcata.2004.03.010
Publication status	Published - 2004 Jul 12

Keywords

Asymmetric autocatalysis
Asymmetric synthesis
Crystals
Enantiomorphism
Surface

ASJC Scopus subject areas

Catalysis
Process Chemistry and Technology
Physical and Theoretical Chemistry

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title = "Highly enantioselective asymmetric autocatalysis induced by chiral ionic crystals of sodium chlorate and sodium bromate",

abstract = "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.",

keywords = "Asymmetric autocatalysis, Asymmetric synthesis, Crystals, Enantiomorphism, Surface",

author = "Itaru Sato and Kousuke Kadowaki and Yasushi Ohgo and Kenso Soai",

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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

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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