The Synthesis of Hydrobenzoin-Based Monoaza Crown Ethers and Their Application as Recyclable Enantioselective Catalysts

Tamás Nemcsok, Zsolt Rapi, Péter Bagi, Attila Oláh, György Keglevich, Péter Bakó

Research output: Contribution to journalArticle

Abstract

Abstract: New recyclable monoaza-15-crown ethers have been synthesized starting from (R,R)-(+)- and (S,S)-(−)-hydrobenzoin. These macrocycles proved to be efficient and reusable phase transfer catalysts in a few asymmetric reactions under mild conditions. The asymmetric epoxidation of trans-chalcone took place with up to 81% ee, while using other chalcone derivatives, the products were formed with 68–88% ee. The hydrobenzoin-based lariat ethers were also tested in the cyclopropanation of a few electron deficient olefins using diethyl bromomalonate to afford the product with good enantioselectivities (54–75% ee). The catalysts were recovered by salt formation, followed by extraction, and were reused without the loss of the activity and effect on the enantioselectivity. Graphic Abstract: The synthesis of hydrobenzoin-based monaza crown ethers and their application as recyclable enantioselective catalysts.[Figure not available: see fulltext.]

Original languageEnglish
JournalCatalysis Letters
DOIs
Publication statusAccepted/In press - Jan 1 2019

Fingerprint

Crown Ethers
Crown ethers
Chalcone
Enantioselectivity
Catalysts
Ethers
Epoxidation
Alkenes
Olefins
Salts
Derivatives
Electrons
hydrobenzoin

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

The Synthesis of Hydrobenzoin-Based Monoaza Crown Ethers and Their Application as Recyclable Enantioselective Catalysts. / Nemcsok, Tamás; Rapi, Zsolt; Bagi, Péter; Oláh, Attila; Keglevich, György; Bakó, Péter.

In: Catalysis Letters, 01.01.2019.

Research output: Contribution to journalArticle

@article{d7ef78c1bc2546af948d9b19e8372a27,
title = "The Synthesis of Hydrobenzoin-Based Monoaza Crown Ethers and Their Application as Recyclable Enantioselective Catalysts",
abstract = "Abstract: New recyclable monoaza-15-crown ethers have been synthesized starting from (R,R)-(+)- and (S,S)-(−)-hydrobenzoin. These macrocycles proved to be efficient and reusable phase transfer catalysts in a few asymmetric reactions under mild conditions. The asymmetric epoxidation of trans-chalcone took place with up to 81{\%} ee, while using other chalcone derivatives, the products were formed with 68–88{\%} ee. The hydrobenzoin-based lariat ethers were also tested in the cyclopropanation of a few electron deficient olefins using diethyl bromomalonate to afford the product with good enantioselectivities (54–75{\%} ee). The catalysts were recovered by salt formation, followed by extraction, and were reused without the loss of the activity and effect on the enantioselectivity. Graphic Abstract: The synthesis of hydrobenzoin-based monaza crown ethers and their application as recyclable enantioselective catalysts.[Figure not available: see fulltext.]",
author = "Tam{\'a}s Nemcsok and Zsolt Rapi and P{\'e}ter Bagi and Attila Ol{\'a}h and Gy{\"o}rgy Keglevich and P{\'e}ter Bak{\'o}",
year = "2019",
month = "1",
day = "1",
doi = "10.1007/s10562-019-03013-0",
language = "English",
journal = "Catalysis Letters",
issn = "1011-372X",
publisher = "Springer Netherlands",

}

TY - JOUR

T1 - The Synthesis of Hydrobenzoin-Based Monoaza Crown Ethers and Their Application as Recyclable Enantioselective Catalysts

AU - Nemcsok, Tamás

AU - Rapi, Zsolt

AU - Bagi, Péter

AU - Oláh, Attila

AU - Keglevich, György

AU - Bakó, Péter

PY - 2019/1/1

Y1 - 2019/1/1

N2 - Abstract: New recyclable monoaza-15-crown ethers have been synthesized starting from (R,R)-(+)- and (S,S)-(−)-hydrobenzoin. These macrocycles proved to be efficient and reusable phase transfer catalysts in a few asymmetric reactions under mild conditions. The asymmetric epoxidation of trans-chalcone took place with up to 81% ee, while using other chalcone derivatives, the products were formed with 68–88% ee. The hydrobenzoin-based lariat ethers were also tested in the cyclopropanation of a few electron deficient olefins using diethyl bromomalonate to afford the product with good enantioselectivities (54–75% ee). The catalysts were recovered by salt formation, followed by extraction, and were reused without the loss of the activity and effect on the enantioselectivity. Graphic Abstract: The synthesis of hydrobenzoin-based monaza crown ethers and their application as recyclable enantioselective catalysts.[Figure not available: see fulltext.]

AB - Abstract: New recyclable monoaza-15-crown ethers have been synthesized starting from (R,R)-(+)- and (S,S)-(−)-hydrobenzoin. These macrocycles proved to be efficient and reusable phase transfer catalysts in a few asymmetric reactions under mild conditions. The asymmetric epoxidation of trans-chalcone took place with up to 81% ee, while using other chalcone derivatives, the products were formed with 68–88% ee. The hydrobenzoin-based lariat ethers were also tested in the cyclopropanation of a few electron deficient olefins using diethyl bromomalonate to afford the product with good enantioselectivities (54–75% ee). The catalysts were recovered by salt formation, followed by extraction, and were reused without the loss of the activity and effect on the enantioselectivity. Graphic Abstract: The synthesis of hydrobenzoin-based monaza crown ethers and their application as recyclable enantioselective catalysts.[Figure not available: see fulltext.]

UR - http://www.scopus.com/inward/record.url?scp=85075217017&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85075217017&partnerID=8YFLogxK

U2 - 10.1007/s10562-019-03013-0

DO - 10.1007/s10562-019-03013-0

M3 - Article

AN - SCOPUS:85075217017

JO - Catalysis Letters

JF - Catalysis Letters

SN - 1011-372X

ER -