Mini-ISES identifies promising carbafructopyranose-based salens for asymmetric catalysis: Tuning ligand shape via the anomeric effect

This study introduces new methods of screening for and tuning chiral space and in so doing identifies a promising set of chiral ligands for asymmetric synthesis. The carbafructopyranosyl-1,2-diamine(s) and salens constructed therefrom are particularly compelling. It is shown that by removing the nat...

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Published inScience advances Vol. 1; no. 6
Main Authors Karukurichi, Kannan R, Fei, Xiang, Swyka, Robert A, Broussy, Sylvain, Shen, Weijun, Dey, Sangeeta, Roy, Sandip K, Berkowitz, David B
Format Journal Article
LanguageEnglish
Published United States American Association for the Advancement of Science 01.07.2015
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Physical Sciences
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Abstract This study introduces new methods of screening for and tuning chiral space and in so doing identifies a promising set of chiral ligands for asymmetric synthesis. The carbafructopyranosyl-1,2-diamine(s) and salens constructed therefrom are particularly compelling. It is shown that by removing the native anomeric effect in this ligand family, one can tune chiral ligand shape and improve chiral bias. This concept is demonstrated by a combination of (i) x-ray crystallographic structure determination, (ii) assessment of catalytic performance, and (iii) consideration of the anomeric effect and its underlying dipolar basis. The title ligands were identified by a new mini version of the in situ enzymatic screening (ISES) procedure through which catalyst-ligand combinations are screened in parallel, and information on relative rate and enantioselectivity is obtained in real time, without the need to quench reactions or draw aliquots. Mini-ISES brings the technique into the nanomole regime (200 to 350 nmol catalyst/20 μml organic volume) commensurate with emerging trends in reaction development/process chemistry. The best-performing β-d-carbafructopyranosyl-1,2-diamine-derived salen ligand discovered here outperforms the best known organometallic and enzymatic catalysts for the hydrolytic kinetic resolution of 3-phenylpropylene oxide, one of several substrates examined for which the ligand is "matched." This ligand scaffold defines a new swath of chiral space, and anomeric effect tunability defines a new concept in shaping that chiral space. Both this ligand set and the anomeric shape-tuning concept are expected to find broad application, given the value of chiral 1,2-diamines and salens constructed from these in asymmetric catalysis.
AbstractList This study introduces new methods of screening for and tuning chiral space and in so doing identifies a promising set of chiral ligands for asymmetric synthesis. The carbafructopyranosyl-1,2-diamine(s) and salens constructed therefrom are particularly compelling. It is shown that by removing the native anomeric effect in this ligand family, one can tune chiral ligand shape and improve chiral bias. This concept is demonstrated by a combination of (i) x-ray crystallographic structure determination, (ii) assessment of catalytic performance, and (iii) consideration of the anomeric effect and its underlying dipolar basis. The title ligands were identified by a new mini version of the in situ enzymatic screening (ISES) procedure through which catalyst-ligand combinations are screened in parallel, and information on relative rate and enantioselectivity is obtained in real time, without the need to quench reactions or draw aliquots. Mini-ISES brings the technique into the nanomole regime (200 to 350 nmol catalyst/20 μml organic volume) commensurate with emerging trends in reaction development/process chemistry. The best-performing β-d-carbafructopyranosyl-1,2-diamine-derived salen ligand discovered here outperforms the best known organometallic and enzymatic catalysts for the hydrolytic kinetic resolution of 3-phenylpropylene oxide, one of several substrates examined for which the ligand is "matched." This ligand scaffold defines a new swath of chiral space, and anomeric effect tunability defines a new concept in shaping that chiral space. Both this ligand set and the anomeric shape-tuning concept are expected to find broad application, given the value of chiral 1,2-diamines and salens constructed from these in asymmetric catalysis.
Enzymes lead to the discovery of new, shape-tunable ligands for controlling catalytic chemistry. This study introduces new methods of screening for and tuning chiral space and in so doing identifies a promising set of chiral ligands for asymmetric synthesis. The carbafructopyranosyl-1,2-diamine(s) and salens constructed therefrom are particularly compelling. It is shown that by removing the native anomeric effect in this ligand family, one can tune chiral ligand shape and improve chiral bias. This concept is demonstrated by a combination of (i) x-ray crystallographic structure determination, (ii) assessment of catalytic performance, and (iii) consideration of the anomeric effect and its underlying dipolar basis. The title ligands were identified by a new mini version of the in situ enzymatic screening (ISES) procedure through which catalyst-ligand combinations are screened in parallel, and information on relative rate and enantioselectivity is obtained in real time, without the need to quench reactions or draw aliquots. Mini-ISES brings the technique into the nanomole regime (200 to 350 nmol catalyst/20 μl organic volume) commensurate with emerging trends in reaction development/process chemistry. The best-performing β- d -carbafructopyranosyl-1,2-diamine–derived salen ligand discovered here outperforms the best known organometallic and enzymatic catalysts for the hydrolytic kinetic resolution of 3-phenylpropylene oxide, one of several substrates examined for which the ligand is “matched.” This ligand scaffold defines a new swath of chiral space, and anomeric effect tunability defines a new concept in shaping that chiral space. Both this ligand set and the anomeric shape-tuning concept are expected to find broad application, given the value of chiral 1,2-diamines and salens constructed from these in asymmetric catalysis.
Author Swyka, Robert A
Broussy, Sylvain
Berkowitz, David B
Dey, Sangeeta
Shen, Weijun
Roy, Sandip K
Fei, Xiang
Karukurichi, Kannan R
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  organization: Department of Chemistry, University of Nebraska, Lincoln, NE 68588-0304, USA
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  organization: Department of Chemistry, University of Nebraska, Lincoln, NE 68588-0304, USA
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  organization: Department of Chemistry, University of Nebraska, Lincoln, NE 68588-0304, USA
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  givenname: David B
  surname: Berkowitz
  fullname: Berkowitz, David B
  organization: Department of Chemistry, University of Nebraska, Lincoln, NE 68588-0304, USA
BackLink https://www.ncbi.nlm.nih.gov/pubmed/26501130$$D View this record in MEDLINE/PubMed
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    fullname: Lichtor P. A.
– volume: 127
  start-page: 8610
  year: 2005
  ident: e_1_3_2_49_2
  article-title: Double-cuvette ISES: In situ estimation of enantioselectivity and relative rate for catalyst screening
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja052010b
  contributor:
    fullname: Dey S.
– volume: 137
  start-page: 2776
  year: 2015
  ident: e_1_3_2_107_2
  article-title: A new class of non-C 2-symmetric ligands for oxidative and redox-neutral palladium-catalyzed asymmetric allylic alkylations of 1,3-diketones
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/jacs.5b00786
  contributor:
    fullname: Trost B. M.
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Snippet This study introduces new methods of screening for and tuning chiral space and in so doing identifies a promising set of chiral ligands for asymmetric...
Enzymes lead to the discovery of new, shape-tunable ligands for controlling catalytic chemistry. This study introduces new methods of screening for and tuning...
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Title Mini-ISES identifies promising carbafructopyranose-based salens for asymmetric catalysis: Tuning ligand shape via the anomeric effect
URI https://www.ncbi.nlm.nih.gov/pubmed/26501130
https://search.proquest.com/docview/1826648716
https://pubmed.ncbi.nlm.nih.gov/PMC4613784
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