Reversal in enantioselectivity induced by achiral alcohols in asymmetric autocatalysis in the presence of a chiral diol as a chiral initiator

Takanori Shibata; Hikaru Tarumi; Tsuneomi Kawasaki; Kenso Soai

doi:10.1016/j.tetasy.2012.07.010

Reversal in enantioselectivity induced by achiral alcohols in asymmetric autocatalysis in the presence of a chiral diol as a chiral initiator

Takanori Shibata, Hikaru Tarumi, Tsuneomi Kawasaki, Kenso Soai

School of Advanced Science and Engineering

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

9 Citations (Scopus)

Abstract

A reversal in enantioselectivity was observed by the combination of a chiral diol and achiral alcohols as a chiral initiator in the asymmetric alkylation of a pyrimidine-5-carbaldehyde using diisopropylzinc. (2S,3S)-Butane-2,3-diol alone induced (R)-pyrimidyl alkanol, while a mixture of the chiral diol and phenol derivatives induced (S)-pyrimidyl alkanol. The effect of achiral alcohols is also discussed.

Original language	English
Pages (from-to)	1023-1027
Number of pages	5
Journal	Tetrahedron Asymmetry
Volume	23
Issue number	14
DOIs	https://doi.org/10.1016/j.tetasy.2012.07.010
Publication status	Published - 2012 Jul 31

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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abstract = "A reversal in enantioselectivity was observed by the combination of a chiral diol and achiral alcohols as a chiral initiator in the asymmetric alkylation of a pyrimidine-5-carbaldehyde using diisopropylzinc. (2S,3S)-Butane-2,3-diol alone induced (R)-pyrimidyl alkanol, while a mixture of the chiral diol and phenol derivatives induced (S)-pyrimidyl alkanol. The effect of achiral alcohols is also discussed.",

author = "Takanori Shibata and Hikaru Tarumi and Tsuneomi Kawasaki and Kenso Soai",

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T1 - Reversal in enantioselectivity induced by achiral alcohols in asymmetric autocatalysis in the presence of a chiral diol as a chiral initiator

AU - Shibata, Takanori

AU - Tarumi, Hikaru

AU - Kawasaki, Tsuneomi

AU - Soai, Kenso

PY - 2012/7/31

Y1 - 2012/7/31

N2 - A reversal in enantioselectivity was observed by the combination of a chiral diol and achiral alcohols as a chiral initiator in the asymmetric alkylation of a pyrimidine-5-carbaldehyde using diisopropylzinc. (2S,3S)-Butane-2,3-diol alone induced (R)-pyrimidyl alkanol, while a mixture of the chiral diol and phenol derivatives induced (S)-pyrimidyl alkanol. The effect of achiral alcohols is also discussed.

AB - A reversal in enantioselectivity was observed by the combination of a chiral diol and achiral alcohols as a chiral initiator in the asymmetric alkylation of a pyrimidine-5-carbaldehyde using diisopropylzinc. (2S,3S)-Butane-2,3-diol alone induced (R)-pyrimidyl alkanol, while a mixture of the chiral diol and phenol derivatives induced (S)-pyrimidyl alkanol. The effect of achiral alcohols is also discussed.

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