R K Dieter

Summary

Affiliation: Clemson University
Country: USA

Publications

  1. ncbi Regio- and stereoselectivity in the reactions of organometallic reagents with an electron-deficient and an electron-rich vinyloxirane: applications for sequential bis-allylic substitution reactions in the generation of vicinal stereogenic centers
    R Karl Dieter
    Hunter Laboratory, Department of Chemistry, Clemson University, Clemson, South Carolina 29634 0973, United States
    J Org Chem 77:4949-67. 2012
  2. ncbi Conjugate addition reactions of N-carbamoyl-4-pyridones with organometallic reagents
    R Karl Dieter
    Department of Chemistry, Hunter Laboratory, Clemson University, Clemson, South Carolina 29634 0973, USA
    J Org Chem 74:3843-8. 2009
  3. ncbi Tandem regio- and stereoselective organocuprate-mediated bis-allylic substitutions
    R Karl Dieter
    Hunter Laboratory, Department of Chemistry, Clemson University, Clemson, South Carolina 29634 0973, USA
    Org Lett 10:2087-90. 2008
  4. ncbi Reaction of alpha-(N-carbamoyl)alkylcuprates with enantioenriched propargyl electrophiles: synthesis of enantioenriched 3-pyrrolines
    R Karl Dieter
    Howard L Hunter Chemistry Laboratory, Clemson University, Clemson, South Carolina 29634 0973, USA
    J Org Chem 71:8755-60. 2006
  5. ncbi A rapid divergent synthesis of highly substituted delta-lactones
    R Karl Dieter
    Howard L Hunter Laboratory, Department of Chemistry, Clemson University, Clemson, South Carolina 29634 0973, USA
    Org Lett 8:4779-82. 2006
  6. ncbi Asymmetric synthesis of enantioenriched (+)-elaeokanine A
    R Karl Dieter
    Department of Chemistry, Hunter Laboratory, Clemson University, Clemson, South Carolina 29634 0973, USA
    J Org Chem 71:5674-8. 2006
  7. ncbi A facile synthesis of polysubstituted pyrroles
    R K Dieter
    Howard L Hunter Chemistry Laboratory, Clemson University, Clemson, South Carolina 29634 0973, USA
    Org Lett 2:2283-6. 2000
  8. ncbi Reactivity and enantioselectivity in the reactions of scalemic stereogenic alpha-(N-carbamoyl)alkylcuprates
    R Karl Dieter
    Howard L Hunter Laboratory, Department of Chemistry, Clemson University, Clemson, South Carolina 29634 0973, USA
    J Org Chem 69:3076-86. 2004
  9. ncbi Halogen- and N-haloimide-promoted homo- and heterocoupling of alpha-(N-carbamoyl)alkylcuprates and alpha-(alkoxy)alkylcuprates
    R Karl Dieter
    Department of Chemistry, Hunter Laboratory, Clemson University, Clemson, South Carolina 29634 0973, USA
    J Org Chem 69:2867-70. 2004
  10. ncbi Alpha-(N-carbamoyl)alkylcuprate chemistry in the synthesis of nitrogen heterocycles
    R Karl Dieter
    Howard L Hunter Chemistry Laboratory, Clemson University, Clemson, South Carolina 29634 0973, USA
    J Org Chem 67:847-55. 2002

Research Grants

  1. NEW DEVELOPMENTS IN ORGANOCOPPER CHEMISTRY
    R Dieter; Fiscal Year: 2004

Collaborators

  • Shengjian Li
  • Rhett T Watson
  • Kishan R Chandupatla
  • Vinayak K Gore
  • James P Snyder

Detail Information

Publications15

  1. ncbi Regio- and stereoselectivity in the reactions of organometallic reagents with an electron-deficient and an electron-rich vinyloxirane: applications for sequential bis-allylic substitution reactions in the generation of vicinal stereogenic centers
    R Karl Dieter
    Hunter Laboratory, Department of Chemistry, Clemson University, Clemson, South Carolina 29634 0973, United States
    J Org Chem 77:4949-67. 2012
    ....
  2. ncbi Conjugate addition reactions of N-carbamoyl-4-pyridones with organometallic reagents
    R Karl Dieter
    Department of Chemistry, Hunter Laboratory, Clemson University, Clemson, South Carolina 29634 0973, USA
    J Org Chem 74:3843-8. 2009
    ..An enantioenriched phosphoramidite ligand promotes the copper catalyzed conjugate addition of Et(2)Zn to a N-carbamoyl-4-pyridone with an er of 91.5:8.5...
  3. ncbi Tandem regio- and stereoselective organocuprate-mediated bis-allylic substitutions
    R Karl Dieter
    Hunter Laboratory, Department of Chemistry, Clemson University, Clemson, South Carolina 29634 0973, USA
    Org Lett 10:2087-90. 2008
    ..The methodology should provide a powerful practical strategy for acyclic stereoselection...
  4. ncbi Reaction of alpha-(N-carbamoyl)alkylcuprates with enantioenriched propargyl electrophiles: synthesis of enantioenriched 3-pyrrolines
    R Karl Dieter
    Howard L Hunter Chemistry Laboratory, Clemson University, Clemson, South Carolina 29634 0973, USA
    J Org Chem 71:8755-60. 2006
    ..The synthetic sequence proceeds under optimal conditions with no loss of enantiopurity relative to the starting propargyl alcohols prepared by asymmetric addition of terminal alkynes to aldehydes...
  5. ncbi A rapid divergent synthesis of highly substituted delta-lactones
    R Karl Dieter
    Howard L Hunter Laboratory, Department of Chemistry, Clemson University, Clemson, South Carolina 29634 0973, USA
    Org Lett 8:4779-82. 2006
    ....
  6. ncbi Asymmetric synthesis of enantioenriched (+)-elaeokanine A
    R Karl Dieter
    Department of Chemistry, Hunter Laboratory, Clemson University, Clemson, South Carolina 29634 0973, USA
    J Org Chem 71:5674-8. 2006
    ....
  7. ncbi A facile synthesis of polysubstituted pyrroles
    R K Dieter
    Howard L Hunter Chemistry Laboratory, Clemson University, Clemson, South Carolina 29634 0973, USA
    Org Lett 2:2283-6. 2000
    ..Treatment of the conjugate adducts with PhOH/TMSCl in CH(2)Cl(2) effected carbamate deprotection and cyclization to afford a flexible two-step synthesis of substituted pyrroles...
  8. ncbi Reactivity and enantioselectivity in the reactions of scalemic stereogenic alpha-(N-carbamoyl)alkylcuprates
    R Karl Dieter
    Howard L Hunter Laboratory, Department of Chemistry, Clemson University, Clemson, South Carolina 29634 0973, USA
    J Org Chem 69:3076-86. 2004
    ..g., substitution, conjugate addition). Low enantiomeric ratios are obtained with the alpha-(N-carbamoyl)benzylcuprates. The lithium-copper transmetalation and cuprate vinylation reactions proceed with retention of configuration...
  9. ncbi Halogen- and N-haloimide-promoted homo- and heterocoupling of alpha-(N-carbamoyl)alkylcuprates and alpha-(alkoxy)alkylcuprates
    R Karl Dieter
    Department of Chemistry, Hunter Laboratory, Clemson University, Clemson, South Carolina 29634 0973, USA
    J Org Chem 69:2867-70. 2004
    ..Low enantioselectivity has been achieved in the oxidative coupling of lithium (n-Bu)(2-pyrrolidinyl)cuprate...
  10. ncbi Alpha-(N-carbamoyl)alkylcuprate chemistry in the synthesis of nitrogen heterocycles
    R Karl Dieter
    Howard L Hunter Chemistry Laboratory, Clemson University, Clemson, South Carolina 29634 0973, USA
    J Org Chem 67:847-55. 2002
    ..Utilization of omega-functionalized alpha,eta-ynoates or beta-iodo-alpha,beta-enoates allows for cyclization onto the omega-functionality providing for a synthetic route to quinolizidines...
  11. ncbi Synthesis of 3-pyrrolines, annulated 3-pyrrolines, and pyrroles from alpha-amino allenes
    R K Dieter
    Howard L Hunter Chemistry Laboratory, Clemson University, Clemson, SC 29634 0973, USA
    Org Lett 3:3855-8. 2001
    ..Enantioenriched pyrrolines are readily prepared from scalemic propargyl alcohols. [reaction: see text]..
  12. ncbi Conjugate addition reactions of alpha-aminoalkylcuprates with alpha, beta-alkenyl-, alpha,beta-alkynyl-, alpha,beta-beta,gamma-allenyl-, and alpha,beta-gamma,delta-dienyl carboxylic acid derivatives, nitriles, and sulfoxides
    R K Dieter
    Hunter Laboratory, Department of Chemistry, Clemson University, Clemson, South Carolina 29634 0973, USA
    J Org Chem 65:8715-24. 2000
    ..Deprotection and cyclization of the alkynyl adducts affords pyrrolin-2-ones, while similar treatment of the allenyl adducts affords 4-alkylidine- pyrrolidin-2-ones and pyrrolizidinones...
  13. ncbi Regio- and enantioselective control in the reactions of alpha-(N-carbamoyl)alkylcuprates with allylic phosphates
    R Karl Dieter
    Howard L. Hunter Laboratory, Department of Chemistry, Clemson University, Clemson, SC 29634-1905, USA
    Org Lett 6:763-6. 2004
    ..Excellent enantioselectivities can be achieved with either a scalemic alpha-di[(N-carbamoyl)alkyl]cuprate and an achiral phosphate or with a scalemic allylic phosphate and an achiral cuprate reagent. [reaction: see text]..
  14. ncbi Reaction of alpha-(N-carbamoyl)alkylcuprates with propargyl substrates: synthetic route to alpha-amino allenes and delta3-pyrrolines
    R Karl Dieter
    Department of Chemistry, Howard L. Hunter Laboratory, Clemson University, Clemson, South Carolina 29634-0973, USA
    J Org Chem 70:2109-19. 2005
    ..The alpha-(N-carbamoyl) allenes can be cyclized to 2-oxazolidinones or deprotected to afford the free amines which can be cyclized to Delta(3)-pyrrolines with either AgNO(3) or Ru(3)(CO)(12)...
  15. ncbi Synthesis of (-)-(R)-pyrrolam a and studies on its stability: a caveat on computational methods
    Rhett T Watson
    Department of Chemistry, Hunter Laboratory, Clemson University, Clemson, South Carolina 29634, USA
    J Org Chem 69:6105-14. 2004
    ..The source of the irreversibility was traced to asymmetric charge distribution in the intermediate dienolate anion. The analysis ultimately led to a semiquantitative sketch of the pyrrolam energy surface...

Research Grants4

  1. NEW DEVELOPMENTS IN ORGANOCOPPER CHEMISTRY
    R Dieter; Fiscal Year: 2004
    ..The proposed synthetic routes to pyrrolidine aza sugars will develop the potential synthetic power of alpha-aminoalkylcuprate chemistry. ..