Non-superimposable mirror image crystals of enantiomers by spontaneous resolution and the chiral discrimination mechanism

Muhammad Sohail; Yao Feng Wang; Shao Xiang Wu; Wei Zeng; Ji Yi Guo; Fu Xue Chen

doi:10.1016/j.cclet.2013.04.045

Non-superimposable mirror image crystals of enantiomers by spontaneous resolution and the chiral discrimination mechanism

Muhammad Sohail, Yao Feng Wang, Shao Xiang Wu, Wei Zeng, Ji Yi Guo, Fu Xue Chen^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

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

3 Citations (Scopus)

Abstract

Non-superimposable mirror image crystals of both enantiomers (S/R) of cyclic γ-alkenyl alcohol (2) have been recognized and remarkably identified by the naked eye. More interestingly, both crystals are an outcome of most astonishingly H-bond and intermolecular σ/π-π interactions. They accounted for the relatively rare and less predictable spontaneous resolution with optical purity >99% ee from the racemic mixture. The chiral discrimination mechanism of this spontaneous resolution has also been proposed.

Original language	English
Pages (from-to)	695-698
Number of pages	4
Journal	Chinese Chemical Letters
Volume	24
Issue number	8
DOIs	https://doi.org/10.1016/j.cclet.2013.04.045
Publication status	Published - Aug 2013

Keywords

Mirror images
Octahydrobenzofuran
Preferential crystallization
Spontaneous resolution

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10.1016/j.cclet.2013.04.045

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Sohail, M., Wang, Y. F., Wu, S. X., Zeng, W., Guo, J. Y., & Chen, F. X. (2013). Non-superimposable mirror image crystals of enantiomers by spontaneous resolution and the chiral discrimination mechanism. Chinese Chemical Letters, 24(8), 695-698. https://doi.org/10.1016/j.cclet.2013.04.045

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abstract = "Non-superimposable mirror image crystals of both enantiomers (S/R) of cyclic γ-alkenyl alcohol (2) have been recognized and remarkably identified by the naked eye. More interestingly, both crystals are an outcome of most astonishingly H-bond and intermolecular σ/π-π interactions. They accounted for the relatively rare and less predictable spontaneous resolution with optical purity >99% ee from the racemic mixture. The chiral discrimination mechanism of this spontaneous resolution has also been proposed.",

keywords = "Mirror images, Octahydrobenzofuran, Preferential crystallization, Spontaneous resolution",

author = "Muhammad Sohail and Wang, {Yao Feng} and Wu, {Shao Xiang} and Wei Zeng and Guo, {Ji Yi} and Chen, {Fu Xue}",

year = "2013",

month = aug,

doi = "10.1016/j.cclet.2013.04.045",

language = "English",

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pages = "695--698",

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T1 - Non-superimposable mirror image crystals of enantiomers by spontaneous resolution and the chiral discrimination mechanism

AU - Sohail, Muhammad

AU - Wang, Yao Feng

AU - Wu, Shao Xiang

AU - Zeng, Wei

AU - Guo, Ji Yi

AU - Chen, Fu Xue

PY - 2013/8

Y1 - 2013/8

N2 - Non-superimposable mirror image crystals of both enantiomers (S/R) of cyclic γ-alkenyl alcohol (2) have been recognized and remarkably identified by the naked eye. More interestingly, both crystals are an outcome of most astonishingly H-bond and intermolecular σ/π-π interactions. They accounted for the relatively rare and less predictable spontaneous resolution with optical purity >99% ee from the racemic mixture. The chiral discrimination mechanism of this spontaneous resolution has also been proposed.

AB - Non-superimposable mirror image crystals of both enantiomers (S/R) of cyclic γ-alkenyl alcohol (2) have been recognized and remarkably identified by the naked eye. More interestingly, both crystals are an outcome of most astonishingly H-bond and intermolecular σ/π-π interactions. They accounted for the relatively rare and less predictable spontaneous resolution with optical purity >99% ee from the racemic mixture. The chiral discrimination mechanism of this spontaneous resolution has also been proposed.

KW - Mirror images

KW - Octahydrobenzofuran

KW - Preferential crystallization

KW - Spontaneous resolution

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U2 - 10.1016/j.cclet.2013.04.045

DO - 10.1016/j.cclet.2013.04.045

M3 - Article

AN - SCOPUS:84879970963

SN - 1001-8417

VL - 24

SP - 695

EP - 698

JO - Chinese Chemical Letters

JF - Chinese Chemical Letters

IS - 8

ER -

Non-superimposable mirror image crystals of enantiomers by spontaneous resolution and the chiral discrimination mechanism

Abstract

Keywords

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