A redox-reconfigurable, ambidextrous asymmetric catalyst

Shahab Mortezaei, Noelle R. Catarineu, James Canary

Research output: Contribution to journalArticle

Abstract

A redox-reconfigurable catalyst derived from l-methionine and incorporating catalytic urea groups has been synthesized. This copper complex catalyzes the enantioselective addition of diethyl malonate to trans-β-nitrostyrene. Either enantiomer of the product can be predetermined by selection of the oxidation state of the copper ion. Enantiomeric excesses of up to 72% (S) and 70% (R) were obtained in acetonitrile. The ability of the catalyst to invert enantiomeric preference was reproduced with several different solvents and bases. Facile interconversion between the Cu 2+ and Cu + redox states allowed easy access to both active helical forms of the complex and, therefore, dial-in enantioselectivity.

Original languageEnglish (US)
Pages (from-to)8054-8057
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number19
DOIs
StatePublished - May 16 2012

Fingerprint

Oxidation-Reduction
Copper
Catalysts
Enantiomers
Enantioselectivity
Acetonitrile
Urea
Methionine
Ions
Oxidation
acetonitrile
diethyl malonate

ASJC Scopus subject areas

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

Cite this

A redox-reconfigurable, ambidextrous asymmetric catalyst. / Mortezaei, Shahab; Catarineu, Noelle R.; Canary, James.

In: Journal of the American Chemical Society, Vol. 134, No. 19, 16.05.2012, p. 8054-8057.

Research output: Contribution to journalArticle

Mortezaei, Shahab ; Catarineu, Noelle R. ; Canary, James. / A redox-reconfigurable, ambidextrous asymmetric catalyst. In: Journal of the American Chemical Society. 2012 ; Vol. 134, No. 19. pp. 8054-8057.
@article{5c0efbd733f244a2852d937d988b87ff,
title = "A redox-reconfigurable, ambidextrous asymmetric catalyst",
abstract = "A redox-reconfigurable catalyst derived from l-methionine and incorporating catalytic urea groups has been synthesized. This copper complex catalyzes the enantioselective addition of diethyl malonate to trans-β-nitrostyrene. Either enantiomer of the product can be predetermined by selection of the oxidation state of the copper ion. Enantiomeric excesses of up to 72{\%} (S) and 70{\%} (R) were obtained in acetonitrile. The ability of the catalyst to invert enantiomeric preference was reproduced with several different solvents and bases. Facile interconversion between the Cu 2+ and Cu + redox states allowed easy access to both active helical forms of the complex and, therefore, dial-in enantioselectivity.",
author = "Shahab Mortezaei and Catarineu, {Noelle R.} and James Canary",
year = "2012",
month = "5",
day = "16",
doi = "10.1021/ja302283s",
language = "English (US)",
volume = "134",
pages = "8054--8057",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "19",

}

TY - JOUR

T1 - A redox-reconfigurable, ambidextrous asymmetric catalyst

AU - Mortezaei, Shahab

AU - Catarineu, Noelle R.

AU - Canary, James

PY - 2012/5/16

Y1 - 2012/5/16

N2 - A redox-reconfigurable catalyst derived from l-methionine and incorporating catalytic urea groups has been synthesized. This copper complex catalyzes the enantioselective addition of diethyl malonate to trans-β-nitrostyrene. Either enantiomer of the product can be predetermined by selection of the oxidation state of the copper ion. Enantiomeric excesses of up to 72% (S) and 70% (R) were obtained in acetonitrile. The ability of the catalyst to invert enantiomeric preference was reproduced with several different solvents and bases. Facile interconversion between the Cu 2+ and Cu + redox states allowed easy access to both active helical forms of the complex and, therefore, dial-in enantioselectivity.

AB - A redox-reconfigurable catalyst derived from l-methionine and incorporating catalytic urea groups has been synthesized. This copper complex catalyzes the enantioselective addition of diethyl malonate to trans-β-nitrostyrene. Either enantiomer of the product can be predetermined by selection of the oxidation state of the copper ion. Enantiomeric excesses of up to 72% (S) and 70% (R) were obtained in acetonitrile. The ability of the catalyst to invert enantiomeric preference was reproduced with several different solvents and bases. Facile interconversion between the Cu 2+ and Cu + redox states allowed easy access to both active helical forms of the complex and, therefore, dial-in enantioselectivity.

UR - http://www.scopus.com/inward/record.url?scp=84862095015&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84862095015&partnerID=8YFLogxK

U2 - 10.1021/ja302283s

DO - 10.1021/ja302283s

M3 - Article

VL - 134

SP - 8054

EP - 8057

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 19

ER -