3-Mono-Substituted BINOL Phosphoric Acids as Effective Organocatalysts in Direct Enantioselective Friedel–Crafts-Type Alkylation of N-Unprotected α-Ketiminoester

Ryohei Yonesaki, Yuta Kondo, Walaa Akkad, Masanao Sawa, Kazuhiro Morisaki, Hiroyuki Morimoto, Takashi Ohshima

研究成果: ジャーナルへの寄稿記事

6 引用 (Scopus)

抄録

Although BINOL-derived phosphoric acids are among the most widely used chiral Brønsted acid organocatalysts, their structures are mostly limited to 3,3′-disubstituted ones and simple 3-mono-substituted ones without any polar functionalities on the 3-substituent have not been used in highly enantioselective reactions. This work reports such 3-mono-substituted analogues as effective organocatalysts in direct highly enantioselective Friedel–Crafts-type alkylation of N-unprotected α-ketiminoester. The origin of the observed high enantioselectivity with the 3-mono-substituted catalyst is also discussed.

元の言語英語
ページ(範囲)15211-15214
ページ数4
ジャーナルChemistry - A European Journal
24
発行部数57
DOI
出版物ステータス出版済み - 10 12 2018

Fingerprint

Phosphoric Acids
Enantioselectivity
Alkylation
Phosphoric acid
Catalysts
Acids
naphthol BINOL

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

これを引用

3-Mono-Substituted BINOL Phosphoric Acids as Effective Organocatalysts in Direct Enantioselective Friedel–Crafts-Type Alkylation of N-Unprotected α-Ketiminoester. / Yonesaki, Ryohei; Kondo, Yuta; Akkad, Walaa; Sawa, Masanao; Morisaki, Kazuhiro; Morimoto, Hiroyuki; Ohshima, Takashi.

:: Chemistry - A European Journal, 巻 24, 番号 57, 12.10.2018, p. 15211-15214.

研究成果: ジャーナルへの寄稿記事

@article{b696be2a4c4a4c4e82516fbb28d531b2,
title = "3-Mono-Substituted BINOL Phosphoric Acids as Effective Organocatalysts in Direct Enantioselective Friedel–Crafts-Type Alkylation of N-Unprotected α-Ketiminoester",
abstract = "Although BINOL-derived phosphoric acids are among the most widely used chiral Br{\o}nsted acid organocatalysts, their structures are mostly limited to 3,3′-disubstituted ones and simple 3-mono-substituted ones without any polar functionalities on the 3-substituent have not been used in highly enantioselective reactions. This work reports such 3-mono-substituted analogues as effective organocatalysts in direct highly enantioselective Friedel–Crafts-type alkylation of N-unprotected α-ketiminoester. The origin of the observed high enantioselectivity with the 3-mono-substituted catalyst is also discussed.",
author = "Ryohei Yonesaki and Yuta Kondo and Walaa Akkad and Masanao Sawa and Kazuhiro Morisaki and Hiroyuki Morimoto and Takashi Ohshima",
year = "2018",
month = "10",
day = "12",
doi = "10.1002/chem.201804078",
language = "English",
volume = "24",
pages = "15211--15214",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "57",

}

TY - JOUR

T1 - 3-Mono-Substituted BINOL Phosphoric Acids as Effective Organocatalysts in Direct Enantioselective Friedel–Crafts-Type Alkylation of N-Unprotected α-Ketiminoester

AU - Yonesaki, Ryohei

AU - Kondo, Yuta

AU - Akkad, Walaa

AU - Sawa, Masanao

AU - Morisaki, Kazuhiro

AU - Morimoto, Hiroyuki

AU - Ohshima, Takashi

PY - 2018/10/12

Y1 - 2018/10/12

N2 - Although BINOL-derived phosphoric acids are among the most widely used chiral Brønsted acid organocatalysts, their structures are mostly limited to 3,3′-disubstituted ones and simple 3-mono-substituted ones without any polar functionalities on the 3-substituent have not been used in highly enantioselective reactions. This work reports such 3-mono-substituted analogues as effective organocatalysts in direct highly enantioselective Friedel–Crafts-type alkylation of N-unprotected α-ketiminoester. The origin of the observed high enantioselectivity with the 3-mono-substituted catalyst is also discussed.

AB - Although BINOL-derived phosphoric acids are among the most widely used chiral Brønsted acid organocatalysts, their structures are mostly limited to 3,3′-disubstituted ones and simple 3-mono-substituted ones without any polar functionalities on the 3-substituent have not been used in highly enantioselective reactions. This work reports such 3-mono-substituted analogues as effective organocatalysts in direct highly enantioselective Friedel–Crafts-type alkylation of N-unprotected α-ketiminoester. The origin of the observed high enantioselectivity with the 3-mono-substituted catalyst is also discussed.

UR - http://www.scopus.com/inward/record.url?scp=85052985511&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85052985511&partnerID=8YFLogxK

U2 - 10.1002/chem.201804078

DO - 10.1002/chem.201804078

M3 - Article

C2 - 30098059

AN - SCOPUS:85052985511

VL - 24

SP - 15211

EP - 15214

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 57

ER -