Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid using a chiral N-(2-hydroxymethyl-4-pyrrolidinyl)benzamide template

Jun Ichi Mizoguchi; Yuko Kawanami; Takehiko Wada; Kazuya Kodama; Kinsei Anzai; Toshiharu Yanagi; Yoshihisa Inoue

doi:10.1021/ol062501g

Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid using a chiral N-(2-hydroxymethyl-4-pyrrolidinyl)benzamide template

Jun Ichi Mizoguchi, Yuko Kawanami, Takehiko Wada, Kazuya Kodama, Kinsei Anzai, Toshiharu Yanagi, Yoshihisa Inoue

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

46 Citations (Scopus)

Abstract

(Chemical Equation Presented) Supramolecular enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid (AC) was performed in the presence of (2S,4S)-4-amino-5-chloro-2-methoxy-N-(1-ethyl-2-hydroxymethyl-4- pyrrolidinyl)benzamide (TKS159), and its stereoisomers were employed as chiral templates. The TKS template provides us with a novel hydrogen-bonding and shielding motif for enantioface-selectively binding an AC molecule. Chiral products 2 and 3 were obtained in good enantiomeric excesses (ee's) of 40% and 40%, respectively.

Original language	English
Pages (from-to)	6051-6054
Number of pages	4
Journal	Organic letters
Volume	8
Issue number	26
DOIs	https://doi.org/10.1021/ol062501g
Publication status	Published - 2006 Dec 21
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol062501g

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title = "Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid using a chiral N-(2-hydroxymethyl-4-pyrrolidinyl)benzamide template",

abstract = "(Chemical Equation Presented) Supramolecular enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid (AC) was performed in the presence of (2S,4S)-4-amino-5-chloro-2-methoxy-N-(1-ethyl-2-hydroxymethyl-4- pyrrolidinyl)benzamide (TKS159), and its stereoisomers were employed as chiral templates. The TKS template provides us with a novel hydrogen-bonding and shielding motif for enantioface-selectively binding an AC molecule. Chiral products 2 and 3 were obtained in good enantiomeric excesses (ee's) of 40% and 40%, respectively.",

author = "Mizoguchi, {Jun Ichi} and Yuko Kawanami and Takehiko Wada and Kazuya Kodama and Kinsei Anzai and Toshiharu Yanagi and Yoshihisa Inoue",

year = "2006",

month = dec,

day = "21",

doi = "10.1021/ol062501g",

language = "English",

volume = "8",

pages = "6051--6054",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "26",

}

TY - JOUR

T1 - Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid using a chiral N-(2-hydroxymethyl-4-pyrrolidinyl)benzamide template

AU - Mizoguchi, Jun Ichi

AU - Kawanami, Yuko

AU - Wada, Takehiko

AU - Kodama, Kazuya

AU - Anzai, Kinsei

AU - Yanagi, Toshiharu

AU - Inoue, Yoshihisa

PY - 2006/12/21

Y1 - 2006/12/21

N2 - (Chemical Equation Presented) Supramolecular enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid (AC) was performed in the presence of (2S,4S)-4-amino-5-chloro-2-methoxy-N-(1-ethyl-2-hydroxymethyl-4- pyrrolidinyl)benzamide (TKS159), and its stereoisomers were employed as chiral templates. The TKS template provides us with a novel hydrogen-bonding and shielding motif for enantioface-selectively binding an AC molecule. Chiral products 2 and 3 were obtained in good enantiomeric excesses (ee's) of 40% and 40%, respectively.

AB - (Chemical Equation Presented) Supramolecular enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid (AC) was performed in the presence of (2S,4S)-4-amino-5-chloro-2-methoxy-N-(1-ethyl-2-hydroxymethyl-4- pyrrolidinyl)benzamide (TKS159), and its stereoisomers were employed as chiral templates. The TKS template provides us with a novel hydrogen-bonding and shielding motif for enantioface-selectively binding an AC molecule. Chiral products 2 and 3 were obtained in good enantiomeric excesses (ee's) of 40% and 40%, respectively.

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DO - 10.1021/ol062501g

M3 - Article

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AN - SCOPUS:33846138332

SN - 1523-7060

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SP - 6051

EP - 6054

JO - Organic Letters

JF - Organic Letters

IS - 26

ER -

Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid using a chiral N-(2-hydroxymethyl-4-pyrrolidinyl)benzamide template

Abstract

ASJC Scopus subject areas

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