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

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

56 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
Externally published	Yes

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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10.1016/j.molcata.2004.03.010

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@article{dd7f2743f5c046d48514b11de2d62ed0,

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",

note = "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.",

year = "2004",

month = jul,

day = "12",

doi = "10.1016/j.molcata.2004.03.010",

language = "English",

volume = "216",

pages = "209--214",

journal = "Journal of Molecular Catalysis A: Chemical",

issn = "1381-1169",

publisher = "Elsevier",

number = "2",

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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 -

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

Abstract

Keywords

ASJC Scopus subject areas

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