Self-disproportionation of enantiomers of non-racemic chiral amine derivatives through achiral chromatography

Tsuyoshi Nakamura; Kaori Tateishi; Shiori Tsukagoshi; Saori Hashimoto; Shotaro Watanabe; Vadim A. Soloshonok; José Luis Aceña; Osamu Kitagawa

doi:10.1016/j.tet.2012.03.054

Self-disproportionation of enantiomers of non-racemic chiral amine derivatives through achiral chromatography

Tsuyoshi Nakamura, Kaori Tateishi, Shiori Tsukagoshi, Saori Hashimoto, Shotaro Watanabe, Vadim A. Soloshonok, José Luis Aceña, Osamu Kitagawa

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

58 Citations (Scopus)

Abstract

Efficient self-disproportionation of enantiomers of several non-racemic chiral amines was achieved through conversion to N-acetamides and subsequent MPLC using an achiral column. The MPLC of these non-racemic N-acetamide derivatives gave the chart having a clear boundary between two fractions. Thus, in the less polar fraction, remarkable enantiomer enrichment was observed (>99%ee), while the ee of more polar fraction was considerably reduced. The magnitude of the enantiomer enrichments and depletions strongly depended on substituent on the amino group.

Original language	English
Pages (from-to)	4013-4017
Number of pages	5
Journal	Tetrahedron
Volume	68
Issue number	21
DOIs	https://doi.org/10.1016/j.tet.2012.03.054
Publication status	Published - 2012 May 27

Keywords

Chromatography
Enantiomers
Enrichment
Phenylethylamines
Self-disproportionation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2012.03.054

Cite this

@article{e8bce35ddeda43babba1a59c107bb6ce,

title = "Self-disproportionation of enantiomers of non-racemic chiral amine derivatives through achiral chromatography",

abstract = "Efficient self-disproportionation of enantiomers of several non-racemic chiral amines was achieved through conversion to N-acetamides and subsequent MPLC using an achiral column. The MPLC of these non-racemic N-acetamide derivatives gave the chart having a clear boundary between two fractions. Thus, in the less polar fraction, remarkable enantiomer enrichment was observed (>99%ee), while the ee of more polar fraction was considerably reduced. The magnitude of the enantiomer enrichments and depletions strongly depended on substituent on the amino group.",

keywords = "Chromatography, Enantiomers, Enrichment, Phenylethylamines, Self-disproportionation",

author = "Tsuyoshi Nakamura and Kaori Tateishi and Shiori Tsukagoshi and Saori Hashimoto and Shotaro Watanabe and Soloshonok, {Vadim A.} and Ace{\~n}a, {Jos{\'e} Luis} and Osamu Kitagawa",

year = "2012",

month = may,

day = "27",

doi = "10.1016/j.tet.2012.03.054",

language = "English",

volume = "68",

pages = "4013--4017",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "21",

}

TY - JOUR

T1 - Self-disproportionation of enantiomers of non-racemic chiral amine derivatives through achiral chromatography

AU - Nakamura, Tsuyoshi

AU - Tateishi, Kaori

AU - Tsukagoshi, Shiori

AU - Hashimoto, Saori

AU - Watanabe, Shotaro

AU - Soloshonok, Vadim A.

AU - Aceña, José Luis

AU - Kitagawa, Osamu

PY - 2012/5/27

Y1 - 2012/5/27

N2 - Efficient self-disproportionation of enantiomers of several non-racemic chiral amines was achieved through conversion to N-acetamides and subsequent MPLC using an achiral column. The MPLC of these non-racemic N-acetamide derivatives gave the chart having a clear boundary between two fractions. Thus, in the less polar fraction, remarkable enantiomer enrichment was observed (>99%ee), while the ee of more polar fraction was considerably reduced. The magnitude of the enantiomer enrichments and depletions strongly depended on substituent on the amino group.

AB - Efficient self-disproportionation of enantiomers of several non-racemic chiral amines was achieved through conversion to N-acetamides and subsequent MPLC using an achiral column. The MPLC of these non-racemic N-acetamide derivatives gave the chart having a clear boundary between two fractions. Thus, in the less polar fraction, remarkable enantiomer enrichment was observed (>99%ee), while the ee of more polar fraction was considerably reduced. The magnitude of the enantiomer enrichments and depletions strongly depended on substituent on the amino group.

KW - Chromatography

KW - Enantiomers

KW - Enrichment

KW - Phenylethylamines

KW - Self-disproportionation

UR - http://www.scopus.com/inward/record.url?scp=84860133980&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84860133980&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2012.03.054

DO - 10.1016/j.tet.2012.03.054

M3 - Article

AN - SCOPUS:84860133980

SN - 0040-4020

VL - 68

SP - 4013

EP - 4017

JO - Tetrahedron

JF - Tetrahedron

IS - 21

ER -

Self-disproportionation of enantiomers of non-racemic chiral amine derivatives through achiral chromatography

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this