Search Results - "Sigman, Matthew S"
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Holistic prediction of enantioselectivity in asymmetric catalysis
Published in Nature (London) (01-07-2019)“…When faced with unfamiliar reaction space, synthetic chemists typically apply the reported conditions (reagents, catalyst, solvent and additives) of a…”
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2
Enantioselective construction of remote quaternary stereocentres
Published in Nature (London) (17-04-2014)“…Small molecules that contain all-carbon quaternary stereocentres—carbon atoms bonded to four distinct carbon substituents—are found in many secondary…”
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3
Predictive and mechanistic multivariate linear regression models for reaction development
Published in Chemical science (Cambridge) (07-03-2018)“…Multivariate Linear Regression (MLR) models utilizing computationally-derived and empirically-derived physical organic molecular descriptors are described in…”
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4
Applications of ortho-Quinone Methide Intermediates in Catalysis and Asymmetric Synthesis
Published in Journal of organic chemistry (18-11-2011)“…Ortho-quinone methides are important synthetic intermediates and widely implicated in biological processes. In this Synopsis, recent advances concerning the…”
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5
A synthetic chemist's guide to electroanalytical tools for studying reaction mechanisms
Published in Chemical science (Cambridge) (14-07-2019)“…Monitoring reactive intermediates can provide vital information in the study of synthetic reaction mechanisms, enabling the design of new catalysts and…”
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6
Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners
Published in Chemical reviews (09-03-2011)“…Ranjan et al discuss recent research in transition metal catalyzed cross-coupling reactions. The use of alkyl-organometallics as reaction partners is also…”
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7
Palladium-catalyzed enantioselective Heck alkenylation of acyclic alkenols using a redox-relay strategy
Published in Journal of the American Chemical Society (18-03-2015)“…We report a highly enantioselective intermolecular Heck reaction of alkenyl triflates and acyclic primary or racemic secondary alkenols. The mild reaction…”
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Enantioselective Palladium-Catalyzed Alkenylation of Trisubstituted Alkenols To Form Allylic Quaternary Centers
Published in Journal of the American Chemical Society (02-11-2016)“…In this report, we describe the generation of remote allylic quaternary stereocenters β, γ, and δ relative to a carbonyl in high enantioselectivity. We utilize…”
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9
Integrating Electrochemical and Statistical Analysis Tools for Molecular Design and Mechanistic Understanding
Published in Accounts of chemical research (18-02-2020)“…Conspectus Medicinal chemistry campaigns set the foundation for streamlined molecular design strategies through the development of quantitative…”
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10
Enantioselective construction of remote tertiary carbon–fluorine bonds
Published in Nature chemistry (01-08-2019)“…The carbon–fluorine bond engenders distinctive physicochemical properties and significant changes to general reactivity. The development of catalytic,…”
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11
Univariate classification of phosphine ligation state and reactivity in cross-coupling catalysis
Published in Science (American Association for the Advancement of Science) (15-10-2021)“…Chemists often use statistical analysis of reaction data with molecular descriptors to identify structure-reactivity relationships, which can enable prediction…”
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12
Imparting Catalyst Control upon Classical Palladium-Catalyzed Alkenyl C–H Bond Functionalization Reactions
Published in Accounts of chemical research (19-06-2012)“…The functional group transformations carried out by the palladium-catalyzed Wacker and Heck reactions are radically different, but they are both alkenyl C–H…”
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13
Data Science Meets Physical Organic Chemistry
Published in Accounts of chemical research (05-08-2021)“…Conspectus At the heart of synthetic chemistry is the holy grail of predictable catalyst design. In particular, researchers involved in reaction development in…”
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14
Enantioselective Heck Arylations of Acyclic Alkenyl Alcohols Using a Redox-Relay Strategy
Published in Science (American Association for the Advancement of Science) (14-12-2012)“…Progress in the development of asymmetric Heck couplings of arenes and acyclic olefins has been limited by a tenuous understanding of the factors that dictate…”
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15
Parameterization of phosphine ligands reveals mechanistic pathways and predicts reaction outcomes
Published in Nature chemistry (01-06-2016)“…The mechanistic foundation behind the identity of a phosphine ligand that best promotes a desired reaction outcome is often non-intuitive, and thus has been…”
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16
Nickel-Catalyzed Enantioselective Reductive Cross-Coupling of Styrenyl Aziridines
Published in Journal of the American Chemical Society (26-04-2017)“…A Ni-catalyzed reductive cross-coupling of styrenyl aziridines with aryl iodides is reported. This reaction proceeds by a stereoconvergent mechanism and is…”
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17
Three-Dimensional Correlation of Steric and Electronic Free Energy Relationships Guides Asymmetric Propargylation
Published in Science (American Association for the Advancement of Science) (30-09-2011)“…Chemical reaction outcomes are often rationalized on the basis of independent analyses of steric and electronic effects. We applied three-dimensional free…”
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18
Enantiodivergent Pd-catalyzed C-C bond formation enabled through ligand parameterization
Published in Science (American Association for the Advancement of Science) (09-11-2018)“…Despite the enormous potential for the use of stereospecific cross-coupling reactions to rationally manipulate the three-dimensional structure of organic…”
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19
Palladium-Catalyzed Enantioselective Redox-Relay Heck Arylation of 1,1-Disubstituted Homoallylic Alcohols
Published in Journal of the American Chemical Society (14-09-2016)“…An enantioselective redox-relay oxidative Heck arylation of 1,1-disubstituted alkenes to construct β-stereocenters was developed using a new…”
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20
Synthesis of Highly Functionalized Tri- and Tetrasubstituted Alkenes via Pd-Catalyzed 1,2-Hydrovinylation of Terminal 1,3-Dienes
Published in Journal of the American Chemical Society (21-01-2015)“…An efficient method for the construction of Csp2–Csp3 bond in a regio- and stereoselective fashion involving 1,3-terminal dienes, enol triflates/nonaflates,…”
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