R K Dieter

Summary

Affiliation: Clemson University
Country: USA

Publications

  1. ncbi request reprint 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. doi request reprint 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. doi request reprint 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 request reprint 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 request reprint 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 request reprint 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 request reprint 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 request reprint 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 request reprint 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 request reprint 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

Collaborators

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

Detail Information

Publications15

  1. ncbi request reprint 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. doi request reprint 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. doi request reprint 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 request reprint 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 request reprint 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 request reprint 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 request reprint 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 request reprint 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 request reprint 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 request reprint 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 request reprint 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 request reprint 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 request reprint 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 request reprint 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 request reprint 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. ..