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
N1 - Funding Information:
This research was supported by a Grant-in-Aid for Scientific Research from the Japan Society for the Promotion of Science (JSPS).
Copyright:
Copyright 2019 Elsevier B.V., All rights reserved.
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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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 -