Highly enantioselective asymmetric autocatalysis of pyrimidin-5-yl alkanol induced by chiral 1,3-disubstituted hydrocarbon allenes

Itaru Sato, Yohei Matsueda, Kousuke Kadowaki, Shigeru Yonekubo, Takanori Shibata, Kenso Soai

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

1,3-Disubstituted chiral allenes without any heteroatoms act as chiral initiators in the addition of (i-Pr)2Zn to pyrimidine-5-carbaldehyde to afford, in combination with the subsequent asymmetric autocatalysis, chiral pyrimidin-5-yl alkanols with up to 98% ee. The absolute configuration of the pyrimidin-5-yl alkanol formed depend on that of the chiral allene.

Original languageEnglish
Pages (from-to)3383-3387
Number of pages5
JournalHelvetica Chimica Acta
Volume85
Issue number10
DOIs
Publication statusPublished - 2002
Externally publishedYes

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autocatalysis
pyrimidines
initiators
Hydrocarbons
hydrocarbons
configurations
propadiene
pyrimidine

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Highly enantioselective asymmetric autocatalysis of pyrimidin-5-yl alkanol induced by chiral 1,3-disubstituted hydrocarbon allenes. / Sato, Itaru; Matsueda, Yohei; Kadowaki, Kousuke; Yonekubo, Shigeru; Shibata, Takanori; Soai, Kenso.

In: Helvetica Chimica Acta, Vol. 85, No. 10, 2002, p. 3383-3387.

Research output: Contribution to journalArticle

Sato, Itaru ; Matsueda, Yohei ; Kadowaki, Kousuke ; Yonekubo, Shigeru ; Shibata, Takanori ; Soai, Kenso. / Highly enantioselective asymmetric autocatalysis of pyrimidin-5-yl alkanol induced by chiral 1,3-disubstituted hydrocarbon allenes. In: Helvetica Chimica Acta. 2002 ; Vol. 85, No. 10. pp. 3383-3387.
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