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^*

^*Corresponding author for this work

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

29 Citations (Scopus)

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.

Original language	English
Pages (from-to)	168-169
Number of pages	2
Journal	Chemistry Letters
Issue number	2
DOIs	https://doi.org/10.1246/cl.2002.168
Publication status	Published - 2002 Feb 5
Externally published	Yes

ASJC Scopus subject areas

Chemistry(all)

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10.1246/cl.2002.168

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@article{27c3bb00f5ff46b1895cf6517330bfd3,

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

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",

month = feb,

day = "5",

doi = "10.1246/cl.2002.168",

language = "English",

pages = "168--169",

journal = "Chemistry Letters",

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publisher = "Chemical Society of Japan",

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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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DO - 10.1246/cl.2002.168

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JO - Chemistry Letters

JF - Chemistry Letters

IS - 2

ER -

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

Abstract

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