BLACKMONDLAB

PUBLICATIONS

2009

Zotova, N.; Moran, A.; Armstrong, A.; Blackmond, D.G. A coherent mechanistic rationale for additive effects and autoinductive behaviour in proline-mediated reactions. Adv Synth Catal 2009, 351 (17), 2765-2769.

Zotova, N.; Broadbelt, L.J.; Armstrong, A.; Blackmond, D.G. Kinetic and mechanistic studies of proline-mediated direct intermolecular aldol reactions. Bioorg Med Chem Lett 2009, 19 (14), 3934-7. PMID: 19362473.

Blackmond, D.G. An examination of the role of autocatalytic cycles in the chemistry of proposed primordial reactions. Angew Chem Int Ed Engl 2009, 48 (2), 386-90. PMID: 19053125.

Blackmond, D.G. "If pigs could fly" chemistry: A tutorial on the principle of microscopic reversibility. Angew Chem Int Ed Engl 2009, 48 (15), 2648-54. PMID: 19117002.

Blackmond, D.G. Challenging the concept of "recycling" as a mechanism for the evolution of homochirality in chemical reactions. Chirality 2009, 21 (3), 359-62. PMID: 18570293.

Klussmann, M.; Blackmond, D.G. Origin of homochirality. In: Chemical evolution II: From the origins of life to modern society. American Chemical Society, 2009; Vol. 1025, pp. 133-145.

Izumi, T.; Blackmond, D.G. The double solubility rule holds for racemizing enantiomers. Chemistry 2009, 15 (13), 3065-8. PMID: 19222072.

2008

Viedma, C.; Ortiz, J.E.; de Torres, T.; Izumi, T.; Blackmond, D.G. Evolution of solid phase homochirality for a proteinogenic amino acid. J Am Chem Soc 2008, 130 (46), 15274-5. PMID: 18954052.

Blackmond, D.G. Response to “Comment on 'A re-examination of reversibility in reaction models for the spontaneous emergence of homochirality'”. J Phys Chem B 2008, 112 (31), 9553-9555.

Blackmond, D.G.; Matar, O.K. Re-examination of reversibility in reaction models for the spontaneous emergence of homochirality. J Phys Chem B 2008, 112 (16), 5098-104. PMID: 18370430.

Ferretti, A.C.; Mathew, J.S.; Ashworth, I.; Purdy, M.; Brennan, C.; Blackmond, D.G. Mechanistic inferences derived from competitive catalytic reactions: Pd(binap)-catalyzed amination of aryl halides. Adv Synth Catal 2008, 350 (7-8), 1007-1012.

Noorduin, W.L.; Izumi, T.; Millemaggi, A.; Leeman, M.; Meekes, H.; Van Enckevort, W.J.; Kellogg, R.M.; Kaptein, B.; Vlieg, E.; Blackmond, D.G. Emergence of a single solid chiral state from a nearly racemic amino acid derivative. J Am Chem Soc 2008, 130 (4), 1158-9. PMID: 18173274.

Zotova, N.; Mathew, S.P.; Iwamura, H.; Blackmond, D.G. Reaction progress kinetic analysis: A powerful methodology for streamlining pharmaceutical reaction steps. In: Process chemistry in the pharmaceutical industry. Eds. K. Gadamasetti; T. Braish. CRC Press, New York, 2008; Vol. 2 - Challenges in an Ever Changing Climate, pp. 455-464.

2007

Zotova, N.; Franzke, A.; Armstrong, A.; Blackmond, D.G. Clarification of the role of water in proline-mediated aldol reactions. J Am Chem Soc 2007, 129 (49), 15100-1. PMID: 18001021.

Blackmond, D.G. Response to “Comments on a possible transition to solid-phase homochirality”. Chem Eur J 2007, 13 (36), 10306-10311.

Klussmann, M.; Izumi, T.; White, A.J.; Armstrong, A.; Blackmond, D.G. Emergence of solution-phase homochirality via crystal engineering of amino acids. J Am Chem Soc 2007, 129 (24), 7657-60. PMID: 17530759.

Ferretti, A.C.; Mathew, J.S.; Blackmond, D.G. Reaction calorimetry as a tool for understanding reaction mechanisms:  application to Pd-catalyzed reactions. Ind Eng Chem Res 2007, 46 (25), 8584-8589.

Blackmond, D.G.; Armstrong, A.; Coombe, V.; Wells, A. Water in organocatalytic processes: debunking the myths. Angew Chem Int Ed Engl 2007, 46 (21), 3798-800. PMID: 17361975.

Blackmond, D.G.; Klussmann, M. Spoilt for choice: Assessing phase behavior models for the evolution of homochirality. Chem Commun (Camb) 2007,  (39), 3990-6. PMID: 17912393.

Blackmond, D.G. "Chiral amnesia" as a driving force for solid-phase homochirality. Chemistry 2007, 13 (12), 3290-5. PMID: 17366493.

Phua, P.H.; Mathew, S.P.; White, A.J.; de Vries, J.G.; Blackmond, D.G.; Hii, K.K. Elucidating the mechanism of the asymmetric aza-Michael reaction. Chemistry 2007, 13 (16), 4602-13. PMID: 17352437.

Blackmond, D.G. Kinetic investigations of the Soai autocatalytic reaction. In: Asymmetric synthesis: The essentials. Eds. M. Christmann; S. Bräse. Wiley, New York, 2007; pp. 181-185.

Blackmond, D.G.; Klussmann, M. Investigating the evolution of biomolecular homochirality. AIChE Journal 2007, 53 (1), 2-8.

2006

Klussmann, M.; Iwamura, H.; Mathew, S.P.; Wells, D.H., Jr.; Pandya, U.; Armstrong, A.; Blackmond, D.G. Thermodynamic control of asymmetric amplification in amino acid catalysis. Nature 2006, 441 (7093), 621-3. PMID: 16738656.

Klussmann, M.; White, A.J.; Armstrong, A.; Blackmond, D.G. Rationalization and prediction of solution enantiomeric excess in ternary phase systems. Angew Chem Int Ed Engl 2006, 45 (47), 7985-9. PMID: 16986192.

Klussmann, M.; Mathew, S.P.; Iwamura, H.; Wells, D.H., Jr.; Armstrong, A.; Blackmond, D.G. Kinetic rationalization of nonlinear effects in asymmetric catalysis based on phase behavior. Angew Chem Int Ed Engl 2006, 45 (47), 7989-92. PMID: 17061299.

Mathew, S.P.; Klussmann, M.; Iwamura, H.; Wells, D.H., Jr.; Armstrong, A.; Blackmond, D.G. A mechanistic rationalization of unusual kinetic behavior in proline-mediated C-O and C-N bond-forming reactions. Chem Commun (Camb) 2006,  (41), 4291-3. PMID: 17047844.

Blackmond, D.G.; Schultz, T.; Mathew, J.S.; Loew, C.; Rosner, T.; Pfaltz, A. Comprehensive kinetic screening of palladium catalysts for Heck reactions. Synlett 2006, 2006 (18), 3135-3139.

Blackmond, D.G.; Hodnett, N.S.; Lloyd-Jones, G.C. Mechanistic implications of pseudo zero order kinetics in kinetic resolutions. J Am Chem Soc 2006, 128 (23), 7450-1. PMID: 16756293.

Mathew, J.S.; Klussmann, M.; Iwamura, H.; Valera, F.; Futran, A.; Emanuelsson, E.A.; Blackmond, D.G. Investigations of Pd-catalyzed ArX coupling reactions informed by reaction progress kinetic analysis. J Org Chem 2006, 71 (13), 4711-22. PMID: 16776495.

Shekhar, S.; Ryberg, P.; Hartwig, J.F.; Mathew, J.S.; Blackmond, D.G.; Strieter, E.R.; Buchwald, S.L. Reevaluation of the mechanism of the amination of aryl halides catalyzed by BINAP-ligated palladium complexes. J Am Chem Soc 2006, 128 (11), 3584-91. PMID: 16536531.

Blackmond, D.G. Mechanistic study of the Soai autocatalytic reaction informed by kinetic analysis. Tetrahedron: Asymmetry 2006, 17 (4), 584-589.

Blackmond, D.G.; Ropic, M.; Stefinovic, M. Kinetic studies of the asymmetric transfer hydrogenation of imines with formic acid catalyzed by Rh−diamine catalysts. Org Process Res Dev 2006, 10 (3), 457-463.

2005

Blackmond, D.G. Kinetic investigations of the role of catalysis in the origin of biological Homochirality. Strem Chemiker 2005, XXII (1), 14-23.

Blackmond, D.G. Reaction progress kinetic analysis: a powerful methodology for mechanistic studies of complex catalytic reactions. Angew Chem Int Ed Engl 2005, 44 (28), 4302-20. PMID: 15997457.

Mathew, S.P.; Gunathilagan, S.; Roberts, S.M.; Blackmond, D.G. Mechanistic insights from reaction progress kinetic analysis of the polypeptide-catalyzed epoxidation of chalcone. Org Lett 2005, 7 (22), 4847-50. PMID: 16235904.

Reetz, M.T.; Meiswinkel, A.; Mehler, G.; Angermund, K.; Graf, M.; Thiel, W.; Mynott, R.; Blackmond, D.G. Why are BINOL-based monophosphites such efficient ligands in Rh-catalyzed asymmetric olefin hydrogenation? J Am Chem Soc 2005, 127 (29), 10305-13. PMID: 16028942.

Arseniyadis, S.; Subhash, P.V.; Valleix, A.; Mathew, S.P.; Blackmond, D.G.; Wagner, A.; Mioskowski, C. Tuning the enantioselective N-acetylation of racemic amines: a spectacular salt effect. J Am Chem Soc 2005, 127 (17), 6138-9. PMID: 15853296.

Strieter, E.R.; Blackmond, D.G.; Buchwald, S.L. The role of chelating diamine ligands in the Goldberg reaction: a kinetic study on the copper-catalyzed amidation of aryl iodides. J Am Chem Soc 2005, 127 (12), 4120-1. PMID: 15783164.

2004

Iwamura, H.; Wells, D.H., Jr.; Mathew, S.P.; Klussmann, M.; Armstrong, A.; Blackmond, D.G. Probing the active catalyst in product-accelerated proline-mediated reactions. J Am Chem Soc 2004, 126 (50), 16312-3. PMID: 15600319.

Iwamura, H.; Mathew, S.P.; Blackmond, D.G. In situ catalyst improvement in the proline-mediated alpha-amination of aldehydes. J Am Chem Soc 2004, 126 (38), 11770-1. PMID: 15382893.

Mathew, S.P.; Iwamura, H.; Blackmond, D.G. Amplification of enantiomeric excess in a proline-mediated reaction. Angew Chem Int Ed Engl 2004, 43 (25), 3317-21. PMID: 15213963.

Blackmond, D.G. Asymmetric autocatalysis and its implications for the origin of homochirality. Proc Natl Acad Sci USA 2004, 101 (16), 5732-6. PMID: 15067112.

Buono, F.G.; Iwamura, H.; Blackmond, D.G. Physical and chemical rationalization for asymmetric amplification in autocatalytic reactions. Angew Chem Int Ed Engl 2004, 43 (16), 2099-103. PMID: 15083455.

Nielsen, L.P.; Stevenson, C.P.; Blackmond, D.G.; Jacobsen, E.N. Mechanistic investigation leads to a synthetic improvement in the hydrolytic kinetic resolution of terminal epoxides. J Am Chem Soc 2004, 126 (5), 1360-2. PMID: 14759192.

LeBars, J.; Dini, S.; Hawkins, J.M.; Blackmond, D.G. Mechanistic insights into anomalous kinetic behaviour in the hydrogenation of a substituted nitrobenzene. Adv Synth Catal 2004, 346 (8), 943-946.

Richards, S.; Ropic, M.; Blackmond, D.; Walmsley, A. Quantitative determination of the catalysed asymmetric transfer hydrogenation of 1-methyl-6,7-dimethoxy-3,4-dihydroisoquinoline using in situ FTIR and multivariate curve resolution. Anal Chim Acta 2004, 519 (1), 1-9.

2003

Strieter, E.R.; Blackmond, D.G.; Buchwald, S.L. Insights into the origin of high activity and stability of catalysts derived from bulky, electron-rich monophosphinobiaryl ligands in the Pd-catalyzed C-N bond formation. J Am Chem Soc 2003, 125 (46), 13978-80. PMID: 14611232.

Buono, F.G.; Blackmond, D.G. Kinetic evidence for a tetrameric transition state in the asymmetric autocatalytic alkylation of pyrimidyl aldehydes. J Am Chem Soc 2003, 125 (30), 8978-9. PMID: 15369330.

2002

Singh, U.K.; Strieter, E.R.; Blackmond, D.G.; Buchwald, S.L. Mechanistic insights into the Pd(BINAP)-catalyzed amination of aryl bromides: kinetic studies under synthetically relevant conditions. J Am Chem Soc 2002, 124 (47), 14104-14. PMID: 12440909.

Buono, F.; Walsh, P.J.; Blackmond, D.G. Rationalization of anomalous nonlinear effects in the alkylation of substituted benzaldehydes. J Am Chem Soc 2002, 124 (46), 13652-3. PMID: 12431076.

Blackmond, D.G. Requiem for the reaction rate equation? Catal Letters 2002, 83 (3), 133-136.

Blackmond, D.G. Description of the condition for asymmetric amplification in autocatalytic reactions. Adv Synth Catal 2002, 344 (2), 156-158.

2001

Blackmond, D.G.; McMillan, C.R.; Ramdeehul, S.; Schorm, A.; Brown, J.M. Origins of asymmetric amplification in autocatalytic alkylzinc additions. J Am Chem Soc 2001, 123 (41), 10103-4. PMID: 11592892.

Blackmond, D.G. Kinetic resolution using enantioimpure catalysts: mechanistic considerations of complex rate laws. J Am Chem Soc 2001, 123 (4), 545-53. PMID: 11456566.

Rosner, T.; Pfaltz, A.; Blackmond, D.G. Observation of unusual kinetics in Heck reactions of aryl halides: the role of non-steady-state catalyst concentration. J Am Chem Soc 2001, 123 (19), 4621-2. PMID: 11457257.

Rosner, T.; Le Bars, J.; Pfaltz, A.; Blackmond, D.G. Kinetic studies of Heck coupling reactions using palladacycle catalysts: experimental and kinetic modeling of the role of dimer species. J Am Chem Soc 2001, 123 (9), 1848-55. PMID: 11456804.

Le Bars, J.; Häußner, T.; Lang, J.; Pfaltz, A.; Blackmond, D.G. A scale-transparent reaction calorimetric assay for rapid catalyst selection. Adv Synth Catal 2001, 343 (2), 207-214.

2000

Rosner, T.; Sears, P.J.; Nugent, W.A.; Blackmond, D.G. Kinetic investigations of product inhibition in the amino alcohol-catalyzed asymmetric alkylation of benzaldehyde with diethylzinc. Org Lett 2000, 2 (16), 2511-3. PMID: 10956534.

Blackmond, D.G. Kinetic aspects of nonlinear effects in asymmetric catalysis. Acc Chem Res 2000, 33 (6), 402-11. PMID: 10891058.

Blackmond, D.G.; Lightfoot, A.; Pfaltz, A.; Rosner, T.; Schnider, P.; Zimmermann, N. Enantioselective hydrogenation of olefins with phosphinooxazoline-iridium catalysts. Chirality 2000, 12 (5-6), 442-9. PMID: 10824167.