Prediction of Soai reaction enantioselectivity induced by crystals of N -(2-thienylcarbonyl)glycine

Damien J. Carter; Andrew L. Rohl; Alexander Shtukenberg; Shudan Bian; Chunhua Hu; Lisa Baylon; Bart Kahr; Hiroko Mineki; Koichiro Abe; Tsuneomi Kawasaki; Kenso Soai

doi:10.1021/cg300207d

Prediction of Soai reaction enantioselectivity induced by crystals of N -(2-thienylcarbonyl)glycine

Damien J. Carter, Andrew L. Rohl, Alexander Shtukenberg, Shudan Bian, Chunhua Hu, Lisa Baylon, Bart Kahr, Hiroko Mineki, Koichiro Abe, Tsuneomi Kawasaki, Kenso Soai

Chemistry

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

Abstract

The enantioselectivity of the autocatalytic alkylation of 2-tert-butylpyrimidyl-5-carbaldehyde, initiated by chiral crystals of N-(2-thienylcarbonyl)glycine, is predicted computationally. The results are in accord with the correlation of the stereochemical outcome of the reaction and the absolute structure of the crystals determined by the anomalous dispersion of X-rays and circular dichroism spectroscopy.

Original language	English (US)
Pages (from-to)	2138-2145
Number of pages	8
Journal	Crystal Growth and Design
Volume	12
Issue number	4
DOIs	https://doi.org/10.1021/cg300207d
State	Published - Apr 4 2012

ASJC Scopus subject areas

General Chemistry
General Materials Science
Condensed Matter Physics

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10.1021/cg300207d

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title = "Prediction of Soai reaction enantioselectivity induced by crystals of N -(2-thienylcarbonyl)glycine",

abstract = "The enantioselectivity of the autocatalytic alkylation of 2-tert-butylpyrimidyl-5-carbaldehyde, initiated by chiral crystals of N-(2-thienylcarbonyl)glycine, is predicted computationally. The results are in accord with the correlation of the stereochemical outcome of the reaction and the absolute structure of the crystals determined by the anomalous dispersion of X-rays and circular dichroism spectroscopy.",

author = "Carter, {Damien J.} and Rohl, {Andrew L.} and Alexander Shtukenberg and Shudan Bian and Chunhua Hu and Lisa Baylon and Bart Kahr and Hiroko Mineki and Koichiro Abe and Tsuneomi Kawasaki and Kenso Soai",

year = "2012",

month = apr,

day = "4",

doi = "10.1021/cg300207d",

language = "English (US)",

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journal = "Crystal Growth and Design",

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publisher = "American Chemical Society",

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TY - JOUR

T1 - Prediction of Soai reaction enantioselectivity induced by crystals of N -(2-thienylcarbonyl)glycine

AU - Carter, Damien J.

AU - Rohl, Andrew L.

AU - Shtukenberg, Alexander

AU - Bian, Shudan

AU - Hu, Chunhua

AU - Baylon, Lisa

AU - Kahr, Bart

AU - Mineki, Hiroko

AU - Abe, Koichiro

AU - Kawasaki, Tsuneomi

AU - Soai, Kenso

PY - 2012/4/4

Y1 - 2012/4/4

N2 - The enantioselectivity of the autocatalytic alkylation of 2-tert-butylpyrimidyl-5-carbaldehyde, initiated by chiral crystals of N-(2-thienylcarbonyl)glycine, is predicted computationally. The results are in accord with the correlation of the stereochemical outcome of the reaction and the absolute structure of the crystals determined by the anomalous dispersion of X-rays and circular dichroism spectroscopy.

AB - The enantioselectivity of the autocatalytic alkylation of 2-tert-butylpyrimidyl-5-carbaldehyde, initiated by chiral crystals of N-(2-thienylcarbonyl)glycine, is predicted computationally. The results are in accord with the correlation of the stereochemical outcome of the reaction and the absolute structure of the crystals determined by the anomalous dispersion of X-rays and circular dichroism spectroscopy.

UR - http://www.scopus.com/inward/record.url?scp=84859376181&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84859376181&partnerID=8YFLogxK

U2 - 10.1021/cg300207d

DO - 10.1021/cg300207d

M3 - Article

AN - SCOPUS:84859376181

SN - 1528-7483

VL - 12

SP - 2138

EP - 2145

JO - Crystal Growth and Design

JF - Crystal Growth and Design

IS - 4

ER -

Prediction of Soai reaction enantioselectivity induced by crystals of N -(2-thienylcarbonyl)glycine

Abstract

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