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 journalArticle

38 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 languageEnglish
Pages (from-to)13294-13297
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number36
DOIs
Publication statusPublished - Sep 11 2013
Externally publishedYes

Fingerprint

Hydantoins
Chirality
Amino acids
Esters
Carbon
Derivatives
Data storage equipment
Amino Acids

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Asymmetric α-arylation of amino acid derivatives by clayden rearrangement of ester enolates via memory of chirality. / Tomohara, Keisuke; Yoshimura, Tomoyuki; Hyakutake, Ryuichi; Yang, Pan; Kawabata, Takeo.

In: Journal of the American Chemical Society, Vol. 135, No. 36, 11.09.2013, p. 13294-13297.

Research output: Contribution to journalArticle

Tomohara, Keisuke ; Yoshimura, Tomoyuki ; Hyakutake, Ryuichi ; Yang, Pan ; Kawabata, Takeo. / Asymmetric α-arylation of amino acid derivatives by clayden rearrangement of ester enolates via memory of chirality. In: Journal of the American Chemical Society. 2013 ; Vol. 135, No. 36. pp. 13294-13297.
@article{c400419f82d8426281dbf31e751a72bd,
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",
year = "2013",
month = "9",
day = "11",
doi = "10.1021/ja406653n",
language = "English",
volume = "135",
pages = "13294--13297",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "36",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=84884178706&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84884178706&partnerID=8YFLogxK

U2 - 10.1021/ja406653n

DO - 10.1021/ja406653n

M3 - Article

VL - 135

SP - 13294

EP - 13297

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 36

ER -