Enhancement of enantiocontrol/diastereocontrol in catalytic intramolecular cyclopropanation and carbon-hydrogen insertion reactions of diazoacetates with Rh2(4S-MPPIM)4
Tetrahedron LettersPublished 1 October 1995
Michael P. Doyle, Qi‐Lin Zhou, Alexey B. Dyatkin, Daniel A. Ruppar
Citations80
SJR quartileQ3
SJR score0.33
SNIP0.43
Generate an AI Snapshot to get a quick, structured summary of this paper.
Study Snapshot
ObjectiveStudy objective
MethodsResearch methodology
PopulationPopulation studied
Sample sizeSample sizes
OutcomesStudy outcomes here
ResultsStudy results comes here
LimitationsResearch study limitations comes here
A concise AI-generated summary of the paper will appear here once you click Generate AI Snapshot.
TL;DR
Dirhodium(II) tetrakis provides significant enhancement in enantiocontrol for intramolecular cyclopropanation reactions of allylic diazoacetates and optimal enantiOControl/diastereocontroll for intramsolecular C-H insertion reactions of secondary alkyl diazosacetates.
Abstract
Dirhodium(II) tetrakis[methyl 1-(3-phenylpropanoyl)imidazolidin-2-one-4(S)-carboxylate], Rh2(4S-MPPIM) 4, provides significant enhancement in enantiocontrol for intramolecular cyclopropanation reactions of allylic diazoacetates and optimal enantiocontrol/diastereocontrol for intramolecular C-H insertion reactions of secondary alkyl diazoacetates.
Keywords
Chemistry
Journal of the American Chemical SocietyDirhodium(II) tetrakis(carboxamidates) with chiral ligands. Structure and selectivity in catalytic metal-carbene transformations
246 Citations1993Michael P. Doyle, William R. Winchester +4 more
Journal of the American Chemical SocietyEnantioselective Intramolecular Cyclopropanations of Allylic and Homoallylic Diazoacetates and Diazoacetamides Using Chiral Dirhodium(II) Carboxamide Catalysts
215 Citations1995Michael P. Doyle, Richard E. Austin +7 more
Journal of the American Chemical SocietyHigh enantioselectivity in the intramolecular cyclopropanation of allyl diazoacetates using a novel rhodium(II) catalyst
198 Citations1991Michael P. Doyle, Roland J. Pieters +4 more
Journal of the American Chemical SocietyAsymmetric synthesis of lactones with high enantioselectivity by intramolecular carbon-hydrogen insertion reactions of alkyl diazoacetates catalyzed by chiral rhodium(II) carboxamides
142 Citations1991Michael P. Doyle, Arjan van Oeveren +3 more
Journal of the American Chemical SocietyDiastereocontrol for Highly Enantioselective Carbon-Hydrogen Insertion Reactions of Cycloalkyl Diazoacetates
122 Citations1994Michael P. Doyle, Alexey B. Dyatkin +6 more
Journal of Medicinal Chemistry1,2,3-Trisubstituted cyclopropanes as conformationally restricted peptide isosteres: application to the design and synthesis of novel renin inhibitors
91 Citations1992Stephen F. Martin, Richard E. Austin +7 more
Evaluated the efficacy of 1,2,3-trisubstituted cyclopropanes as rigid replacements of beta-strand secondary structure in pseudopeptidic ligands and found that a significant number of substances inhibited renin at nanomolar concentrations.
TetrahedronCyclopropanes as conformationally restricted peptide isosteres. Design and synthesis of novel collagenase inhibitors
75 Citations1993Stephen F. Martin, Christopher J. Oalmann +1 more
The 1,2,3-trisubstituted cyclopropane derivatives 9 and 10 were prepared as conformationally constrained analogues of the known collagenase inhibitor 8 to give directly the dipeptide analogue 9.
Recueil des Travaux Chimiques des Pays-BasEnhanced enantiocontrol in catalytic metal carbene transformations with dirhodium (II) tetrakis[methyl 2‐oxooxazolidin‐4(S)‐carboxylate], Rh<sub>2</sub>(4S‐MEOX)<sub>4</sub>
71 Citations1995Michael P. Doyle, Alexey B. Dyatkin +7 more
Helvetica Chimica ActaEnantioselective Formation of Bicyclic Lactones by Rhodium‐Catalyzed Intramolecular CH‐insertion reactions
56 Citations1994Paul Müller, Philippe Polleux
Tetrahedron LettersSynthesis of 2-deoxyxylolactone from glycerol derivatives via highly enantioselective carbon-hydrogen insertion reactions
48 Citations1994Michael P. Doyle, Alexey B. Dyatkin +1 more
Tetrahedron LettersEnantioselective, rhodium catalyzed intramolecular cyclopropanations of homoallylic diazoacetates.
48 Citations1992Stephen F. Martin, Christopher J. Oalmann +1 more
The Journal of Organic ChemistryEnantioselective Synthesis of (+)-Presqualene Diphosphate
44 Citations1995Daniel H. Rogers, Eugene C. Yi +1 more