Enantioselective synthesis of substituted α-aminophosphonates catalysed by d-glucose-based crown ethers: Pursuit of the origin of stereoselectivity

Son Truong Pham, Zsolt Rapi, P. Bakó, Imre Petneházy, A. Stirling, Zsuzsa Jászay

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Several monoaza-15-crown-5 type macrocycles annelated to phenyl-β-d-glucopyranoside were applied as chiral catalysts in enantioselective Michael addition of an N-protected aminomethylenephosphonate onto acrylic acid derivatives and trans-β-nitrostyrene. Among these crown ethers, three are new. Michael adducts were formed with good to excellent enantio- and diastereoselectivities. Combined MM and QM calculations have revealed that suitable side arms on the crown ether beneficially affect the position of the central sodium cation, which in turn helps enhance the stereocontrol by allowing a closer contact between substrate and catalyst.

Original languageEnglish
Pages (from-to)14945-14953
Number of pages9
JournalNew Journal of Chemistry
Volume41
Issue number24
DOIs
Publication statusPublished - Jan 1 2017

Fingerprint

Crown Ethers
Stereoselectivity
Crown ethers
Glucose
Catalysts
Enantioselectivity
Acrylics
Cations
Positive ions
Sodium
Derivatives
Acids
Substrates
15-crown-5
acrylic acid

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Materials Chemistry

Cite this

Enantioselective synthesis of substituted α-aminophosphonates catalysed by d-glucose-based crown ethers : Pursuit of the origin of stereoselectivity. / Pham, Son Truong; Rapi, Zsolt; Bakó, P.; Petneházy, Imre; Stirling, A.; Jászay, Zsuzsa.

In: New Journal of Chemistry, Vol. 41, No. 24, 01.01.2017, p. 14945-14953.

Research output: Contribution to journalArticle

@article{1d4f0661e3944e3aac7b1a415abef156,
title = "Enantioselective synthesis of substituted α-aminophosphonates catalysed by d-glucose-based crown ethers: Pursuit of the origin of stereoselectivity",
abstract = "Several monoaza-15-crown-5 type macrocycles annelated to phenyl-β-d-glucopyranoside were applied as chiral catalysts in enantioselective Michael addition of an N-protected aminomethylenephosphonate onto acrylic acid derivatives and trans-β-nitrostyrene. Among these crown ethers, three are new. Michael adducts were formed with good to excellent enantio- and diastereoselectivities. Combined MM and QM calculations have revealed that suitable side arms on the crown ether beneficially affect the position of the central sodium cation, which in turn helps enhance the stereocontrol by allowing a closer contact between substrate and catalyst.",
author = "Pham, {Son Truong} and Zsolt Rapi and P. Bak{\'o} and Imre Petneh{\'a}zy and A. Stirling and Zsuzsa J{\'a}szay",
year = "2017",
month = "1",
day = "1",
doi = "10.1039/c7nj03345a",
language = "English",
volume = "41",
pages = "14945--14953",
journal = "New Journal of Chemistry",
issn = "1144-0546",
publisher = "Royal Society of Chemistry",
number = "24",

}

TY - JOUR

T1 - Enantioselective synthesis of substituted α-aminophosphonates catalysed by d-glucose-based crown ethers

T2 - Pursuit of the origin of stereoselectivity

AU - Pham, Son Truong

AU - Rapi, Zsolt

AU - Bakó, P.

AU - Petneházy, Imre

AU - Stirling, A.

AU - Jászay, Zsuzsa

PY - 2017/1/1

Y1 - 2017/1/1

N2 - Several monoaza-15-crown-5 type macrocycles annelated to phenyl-β-d-glucopyranoside were applied as chiral catalysts in enantioselective Michael addition of an N-protected aminomethylenephosphonate onto acrylic acid derivatives and trans-β-nitrostyrene. Among these crown ethers, three are new. Michael adducts were formed with good to excellent enantio- and diastereoselectivities. Combined MM and QM calculations have revealed that suitable side arms on the crown ether beneficially affect the position of the central sodium cation, which in turn helps enhance the stereocontrol by allowing a closer contact between substrate and catalyst.

AB - Several monoaza-15-crown-5 type macrocycles annelated to phenyl-β-d-glucopyranoside were applied as chiral catalysts in enantioselective Michael addition of an N-protected aminomethylenephosphonate onto acrylic acid derivatives and trans-β-nitrostyrene. Among these crown ethers, three are new. Michael adducts were formed with good to excellent enantio- and diastereoselectivities. Combined MM and QM calculations have revealed that suitable side arms on the crown ether beneficially affect the position of the central sodium cation, which in turn helps enhance the stereocontrol by allowing a closer contact between substrate and catalyst.

UR - http://www.scopus.com/inward/record.url?scp=85037633605&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85037633605&partnerID=8YFLogxK

U2 - 10.1039/c7nj03345a

DO - 10.1039/c7nj03345a

M3 - Article

AN - SCOPUS:85037633605

VL - 41

SP - 14945

EP - 14953

JO - New Journal of Chemistry

JF - New Journal of Chemistry

SN - 1144-0546

IS - 24

ER -