Asymmetric autocatalysis of pyrimidyl alkanol induced by optically active 1,1′-binaphthyl, an atropisomeric hydrocarbon, generated from spontaneous resolution on crystallization

Itaru Sato; Shunji Osanai; Kousuke Kadowaki; Tadashi Sugiyama; Takanori Shibata; Kenso Soai

doi:10.1246/cl.2002.168

Asymmetric autocatalysis of pyrimidyl alkanol induced by optically active 1,1′-binaphthyl, an atropisomeric hydrocarbon, generated from spontaneous resolution on crystallization

Itaru Sato, Shunji Osanai, Kousuke Kadowaki, Tadashi Sugiyama, Takanori Shibata, Kenso Soai^*

^*この研究の対応する著者

研究成果: Article › 査読

11 被引用数 (Scopus)

抄録

An atropisomeric hydrocarbon, (R)-1,1′-binaphthyl, acts as a chiral initiator of asymmetric autocatalysis of pyrimidyl alkanol in the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehyde to afford (S)-5-pyrimidyl alkanol 2 with 96% ee. On the other hand, in the presence of (S)-1,1′-binaphthyl, the reaction affords (R)-2 with 94% ee.

本文言語	English
ページ（範囲）	168-169
ページ数	2
ジャーナル	Chemistry Letters
号	2
DOI	https://doi.org/10.1246/cl.2002.168
出版ステータス	Published - 2002 2月 5
外部発表	はい

ASJC Scopus subject areas

化学 (全般)

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10.1246/cl.2002.168

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abstract = "An atropisomeric hydrocarbon, (R)-1,1′-binaphthyl, acts as a chiral initiator of asymmetric autocatalysis of pyrimidyl alkanol in the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehyde to afford (S)-5-pyrimidyl alkanol 2 with 96% ee. On the other hand, in the presence of (S)-1,1′-binaphthyl, the reaction affords (R)-2 with 94% ee.",

author = "Itaru Sato and Shunji Osanai and Kousuke Kadowaki and Tadashi Sugiyama and Takanori Shibata and Kenso Soai",

year = "2002",

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journal = "Chemistry Letters",

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T1 - Asymmetric autocatalysis of pyrimidyl alkanol induced by optically active 1,1′-binaphthyl, an atropisomeric hydrocarbon, generated from spontaneous resolution on crystallization

AU - Sato, Itaru

AU - Osanai, Shunji

AU - Kadowaki, Kousuke

AU - Sugiyama, Tadashi

AU - Shibata, Takanori

AU - Soai, Kenso

PY - 2002/2/5

Y1 - 2002/2/5

N2 - An atropisomeric hydrocarbon, (R)-1,1′-binaphthyl, acts as a chiral initiator of asymmetric autocatalysis of pyrimidyl alkanol in the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehyde to afford (S)-5-pyrimidyl alkanol 2 with 96% ee. On the other hand, in the presence of (S)-1,1′-binaphthyl, the reaction affords (R)-2 with 94% ee.

AB - An atropisomeric hydrocarbon, (R)-1,1′-binaphthyl, acts as a chiral initiator of asymmetric autocatalysis of pyrimidyl alkanol in the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehyde to afford (S)-5-pyrimidyl alkanol 2 with 96% ee. On the other hand, in the presence of (S)-1,1′-binaphthyl, the reaction affords (R)-2 with 94% ee.

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