Brønsted Acid-Catalysed Epoxide Ring-Opening Using Amine Nucleophiles: A Facile Access to β-Amino Alcohols

Aparna Tyagi; Naveen Yadav; Jabir Khan; Sankalan Mondal; Chinmoy Kumar Hazra

doi:10.1002/asia.202200379

Brønsted Acid-Catalysed Epoxide Ring-Opening Using Amine Nucleophiles: A Facile Access to β-Amino Alcohols

Aparna Tyagi
, Naveen Yadav
, Jabir Khan
, Sankalan Mondal
, Chinmoy Kumar Hazra^*

^*Corresponding author for this work

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

18 Scopus citations

Abstract

A mild, efficient, and metal-free synthetic protocol for the synthesis of β-amino alcohols is reported. The reaction proceeds at room temperature with only 0.5 mol % catalyst loading and affords β-amino alcohol derivatives in excellent yield. This protocol is well-tolerated by a wide range of styrene oxide and aniline derivatives. A notably efficacious gram-scale synthesis is also reported with a high TON=842. Further, the Hammett correlation study was also performed to identify the rate-determining step.

Original language	English
Article number	e202200379
Journal	Chemistry - An Asian Journal
Volume	17
Issue number	14
DOIs	https://doi.org/10.1002/asia.202200379
State	Published - 15 Jul 2022
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2022 Wiley-VCH GmbH.

Keywords

aniline
metal-free
phenyl oxirane
β-amino alcohols

ASJC Scopus subject areas

Biochemistry
Organic Chemistry

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10.1002/asia.202200379

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title = "Br{\o}nsted Acid-Catalysed Epoxide Ring-Opening Using Amine Nucleophiles: A Facile Access to β-Amino Alcohols",

abstract = "A mild, efficient, and metal-free synthetic protocol for the synthesis of β-amino alcohols is reported. The reaction proceeds at room temperature with only 0.5 mol \% catalyst loading and affords β-amino alcohol derivatives in excellent yield. This protocol is well-tolerated by a wide range of styrene oxide and aniline derivatives. A notably efficacious gram-scale synthesis is also reported with a high TON=842. Further, the Hammett correlation study was also performed to identify the rate-determining step.",

keywords = "aniline, metal-free, phenyl oxirane, β-amino alcohols",

author = "Aparna Tyagi and Naveen Yadav and Jabir Khan and Sankalan Mondal and Hazra, \{Chinmoy Kumar\}",

note = "Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH.",

year = "2022",

month = jul,

day = "15",

doi = "10.1002/asia.202200379",

language = "English",

volume = "17",

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T1 - Brønsted Acid-Catalysed Epoxide Ring-Opening Using Amine Nucleophiles

T2 - A Facile Access to β-Amino Alcohols

AU - Tyagi, Aparna

AU - Yadav, Naveen

AU - Khan, Jabir

AU - Mondal, Sankalan

AU - Hazra, Chinmoy Kumar

PY - 2022/7/15

Y1 - 2022/7/15

N2 - A mild, efficient, and metal-free synthetic protocol for the synthesis of β-amino alcohols is reported. The reaction proceeds at room temperature with only 0.5 mol % catalyst loading and affords β-amino alcohol derivatives in excellent yield. This protocol is well-tolerated by a wide range of styrene oxide and aniline derivatives. A notably efficacious gram-scale synthesis is also reported with a high TON=842. Further, the Hammett correlation study was also performed to identify the rate-determining step.

AB - A mild, efficient, and metal-free synthetic protocol for the synthesis of β-amino alcohols is reported. The reaction proceeds at room temperature with only 0.5 mol % catalyst loading and affords β-amino alcohol derivatives in excellent yield. This protocol is well-tolerated by a wide range of styrene oxide and aniline derivatives. A notably efficacious gram-scale synthesis is also reported with a high TON=842. Further, the Hammett correlation study was also performed to identify the rate-determining step.

KW - aniline

KW - metal-free

KW - phenyl oxirane

KW - β-amino alcohols

UR - https://www.scopus.com/pages/publications/85130399013

U2 - 10.1002/asia.202200379

DO - 10.1002/asia.202200379

M3 - Article

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AN - SCOPUS:85130399013

SN - 1861-4728

VL - 17

JO - Chemistry - An Asian Journal

JF - Chemistry - An Asian Journal

IS - 14

M1 - e202200379

ER -

Brønsted Acid-Catalysed Epoxide Ring-Opening Using Amine Nucleophiles: A Facile Access to β-Amino Alcohols

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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