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

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

Fingerprint

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Cite this

Shibata, T., Tarumi, H., Kawasaki, T., & Soai, K. (2012). Reversal in enantioselectivity induced by achiral alcohols in asymmetric autocatalysis in the presence of a chiral diol as a chiral initiator. Tetrahedron Asymmetry, 23(14), 1023-1027. https://doi.org/10.1016/j.tetasy.2012.07.010

@article{5b795634811d4fdc94d19da5e159a49e,

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

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",

year = "2012",

month = jul,

day = "31",

doi = "10.1016/j.tetasy.2012.07.010",

language = "English",

volume = "23",

pages = "1023--1027",

journal = "Tetrahedron Asymmetry",

issn = "0957-4166",

publisher = "Elsevier Limited",

number = "14",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=84865499251&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84865499251&partnerID=8YFLogxK

U2 - 10.1016/j.tetasy.2012.07.010

DO - 10.1016/j.tetasy.2012.07.010

M3 - Article

AN - SCOPUS:84865499251

VL - 23

SP - 1023

EP - 1027

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

SN - 0957-4166

IS - 14

ER -

Access to Document

10.1016/j.tetasy.2012.07.010