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

Research output: Contribution to journalArticle

25 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 languageEnglish
Pages (from-to)168-169
Number of pages2
JournalChemistry Letters
Issue number2
Publication statusPublished - 2002 Feb 5
Externally publishedYes

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Hydrocarbons
Crystallization
pyrimidine

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Asymmetric autocatalysis of pyrimidyl alkanol induced by optically active 1,1′-binaphthyl, an atropisomeric hydrocarbon, generated from spontaneous resolution on crystallization. / Sato, Itaru; Osanai, Shunji; Kadowaki, Kousuke; Sugiyama, Tadashi; Shibata, Takanori; Soai, Kenso.

In: Chemistry Letters, No. 2, 05.02.2002, p. 168-169.

Research output: Contribution to journalArticle

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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.",
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AU - Osanai, Shunji

AU - Kadowaki, Kousuke

AU - Sugiyama, Tadashi

AU - Shibata, Takanori

AU - Soai, Kenso

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