Asymmetric α-arylation of amino acid derivatives by clayden rearrangement of ester enolates via memory of chirality

Keisuke Tomohara; Tomoyuki Yoshimura; Ryuichi Hyakutake; Pan Yang; Takeo Kawabata

doi:10.1021/ja406653n

Asymmetric α-arylation of amino acid derivatives by clayden rearrangement of ester enolates via memory of chirality

Keisuke Tomohara, Tomoyuki Yoshimura, Ryuichi Hyakutake, Pan Yang, Takeo Kawabata

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

46 Citations (Scopus)

Abstract

A method for asymmetric α-arylation of amino acid derivatives has been developed. The arylation was performed by Clayden rearrangement of ester enolates via memory of chirality to give hydantoins with an aryl-substituted tetrasubstituted carbon with up to 99% ee.

Original language	English
Pages (from-to)	13294-13297
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	135
Issue number	36
DOIs	https://doi.org/10.1021/ja406653n
Publication status	Published - Sep 11 2013
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja406653n

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title = "Asymmetric α-arylation of amino acid derivatives by clayden rearrangement of ester enolates via memory of chirality",

abstract = "A method for asymmetric α-arylation of amino acid derivatives has been developed. The arylation was performed by Clayden rearrangement of ester enolates via memory of chirality to give hydantoins with an aryl-substituted tetrasubstituted carbon with up to 99% ee.",

author = "Keisuke Tomohara and Tomoyuki Yoshimura and Ryuichi Hyakutake and Pan Yang and Takeo Kawabata",

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doi = "10.1021/ja406653n",

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T1 - Asymmetric α-arylation of amino acid derivatives by clayden rearrangement of ester enolates via memory of chirality

AU - Tomohara, Keisuke

AU - Yoshimura, Tomoyuki

AU - Hyakutake, Ryuichi

AU - Yang, Pan

AU - Kawabata, Takeo

PY - 2013/9/11

Y1 - 2013/9/11

N2 - A method for asymmetric α-arylation of amino acid derivatives has been developed. The arylation was performed by Clayden rearrangement of ester enolates via memory of chirality to give hydantoins with an aryl-substituted tetrasubstituted carbon with up to 99% ee.

AB - A method for asymmetric α-arylation of amino acid derivatives has been developed. The arylation was performed by Clayden rearrangement of ester enolates via memory of chirality to give hydantoins with an aryl-substituted tetrasubstituted carbon with up to 99% ee.

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Asymmetric α-arylation of amino acid derivatives by clayden rearrangement of ester enolates via memory of chirality

Abstract

All Science Journal Classification (ASJC) codes

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