Associate Professor

Contact Info

Office:
536A
Phone Number:
Other Affiliations:
Education:
  • S.B. Massachusetts Institute of Technology, 2000
  • Ph.D. California Institute of Technology, 2005
  • Postdoc  Stanford University, 2005-2008
Research Areas:
Research Interests:

Organic Chemistry

Research in our group is focused on the development of new synthetic transformations, primarily centered around transition metal catalysis.  Critical to the invention of these methods is our ability to derive inspiration from both reaction mechanisms and natural products.  Our understanding of intermediates along mechanistic pathways allows us to design innovative chemcial transformations that can capitalize on these potentially reactive species.  Concurrently, we are interested in natural products and other molecules possessing interesting structural properties and biological activity.  Our analyses of their respective core molecular architectures initiates the design of these synthetically important methods.  These sources of inspiration continuously feed into our logical advancement of synthetic methods.  At the same time, our expansion of the synthetic toolbox affords us opportunities for applications of these methods, both in mechanistic studies and in natural product synthesis.

Current efforts in our group are primarily dedicated toward three distinct areas: catalytic alkyne activation, directed catalytic C–H functionalization, and light-activated catalysis based on earth-abundant reagents.  In all of these areas, fundamental questions of reaction design and potential applications are probed.  Ultimately, we anticipate that our explorations in these and other conceptual areas will eventually deepen our understanding of many principles of catalysis and reactivity.

Selected Publications:

2017-2018

Wang, J.; Mahajani, M.; Jackson, S. L.; Yang, Y.; Chen, M.; Ferreira, E. M.; Lin, Y.; Yan, Y. Engineering a bacterial platform for total biosynthesis of caffeic acid derived phenethyl esters and amides. Metabolic Engineering 2017, 44, 89-99. doi:10.1016/j.ymben.2017.09.011

Seizert, C. A.; Ferreira, E. M. A boron-based Ireland-Claisen approach to the synthesis of pordamacrine A. Tetrahedron 2017, 73(29), 4186-4194. doi:10.1016/j.tet.2016.11.030

Li, Q.; Ferreira, E. M. Meta-Selective C−H Arylation of Aromatic Alcohols with a Readily Attachable and Cleavable Molecular Scaffold. Chemistry - A European Journal 2017, 23(48), 11519-11523. doi:10.1002/chem.201703054

Sarabia, F. J.; Ferreira, E. M. Radical Cation Cyclopropanations via Chromium Photooxidative Catalysis. Organic Letters 2017, 19(11), 2865-2868. doi:10.1021/acs.orglett.7b01095

Stevenson, S. M.; Higgins, R. F.; Shores, M. P.; Ferreira, E. M. Chromium photocatalysis: accessing structural complements to Diels-Alder adducts with electron-deficient dienophiles. Chemical Science 2017, 8(1), 654-660. doi:10.1039/c6sc03303b

Huynh, K. Q.; Seizert, C. A.; Ozumerzifon, T. J.; Allegretti, P. A.; Ferreira, E. M. Platinum-Catalyzed α,β-Unsaturated Carbene Formation in the Formal Syntheses of Frondosin B and Liphagal. Organic Letters 2017, 19(1), 294-297. http://doi.org/10.1021/acs.orglett.6b03682

2016

Stevenson, S. M.; Newcomb, E. T.; Ferreira, E. M. C–C Bond Migration in the Cycloisomerization of 1,6-Enynes. Organic Chemistry Frontiers 2016, 3, 1228-1335. http://doi.org/10.1039/c6qo00224b

Li, Q.; Knight, B. J.; Ferreira, E. M. Palladium(II)-Catalyzed ortho-Arylation of Aromatic Alcohols with a Readily Attachable and Cleavable Molecular Scaffold. Chemistry - A European Journal 2016, 22, 13054-13058. http://doi.org/10.1002/chem.201602844

Higgins, R. F.; Fatur, S. M.; Shepard, S. G.; Stevenson, S. M.; Boston, D. J.; Ferreira, E. M.; Damrauer, N. H.; Rappé, A. K.; Shores, M. P. Uncovering the Roles of Oxygen in Cr(III) Photoredox Catalysis. Journal of the American Chemical Society 2016, 138, 5451 - 5464. http://doi.org/10.1021/jacs.6b02723

Newcomb, E. T.; Knutson, P. C.; Pedersen, B. A.; Ferreira, E. M. Total Synthesis of Gelsenicine via a Catalyzed Cycloisomerization Strategy. Journal of the American Chemical Society 2016, 138, 108 - 111. http://doi.org/10.1021/jacs.5b12263

Knight, B. J.; Rothbaum, J. O.; Ferreira, E. M. The design of a readily attachable and cleavable molecular scaffold for ortho-selective C–H alkenylation of arene alcohols. Chem. Sci. 2016, 7, 1982 - 1987. http://doi.org/10.1039/c5sc03948g

Allegretti, P. A.; Huynh, K.; Ozumerzifon, T. J.; Ferreira, E. M. Lewis Acid Mediated Vinylogous Additions of Enol Nucleophiles into an α,β-Unsaturated Platinum Carbene. Organic Letters 2016, 18, 64 - 67. http://doi.org/10.1021/acs.orglett.5b03246

2015

Knight, B. J.; Stache, E. E.; Ferreira, E. M. An analysis of the complementary stereoselective alkylations of imidazolidinone derivatives toward α-quaternary proline-based amino amides. Tetrahedron 2015, 71, 5814 - 5823. http://doi.org/10.1016/j.tet.2015.05.010

Stevenson, S. M.; Shores, M. P.; Ferreira, E. M. Photooxidizing Chromium Catalysts for Promoting Radical Cation Cycloadditions. Angewandte Chemie International Edition 2015, 54, 6506 - 6510. http://doi.org/10.1002/anie.201501220

2014

Knight, B. J.; Stache, E. E.; Ferreira, E. M. Complementary Stereochemical Outcomes in Proline-Based Self-Regenerations of Stereocenters. Organic Letters 2014, 16, 432 - 435. http://doi.org/10.1021/ol403320d

Seizert, C. A.; Ferreira, E. M. An Examination of the Scope and Stereochemistry of the Ireland-Claisen Rearrangement of Boron Ketene Acetals. Chemistry - A European Journal 2014, 20, 4460 - 4468. http://doi.org/10.1002/chem.201304384

Rooke, D. A.; Menard, Z. A.; Ferreira, E. M. An analysis of the influences dictating regioselectivity in platinum-catalyzed hydrosilylations of internal alkynes. Tetrahedron 2014, 70, 4232 - 4244. http://doi.org/10.1016/j.tet.2014.03.012

Stevenson, S. M.; Newcomb, E. T.; Ferreira, E. M. C–C bond migration in the cycloisomerization of oxygen-tethered 1,6-enynes. Chem. Commun. 2014, 50, 5239 - 5241. http://doi.org/10.1039/c3cc47499b

Ferreira, E. M. C–H Activation. A Surrogate for Selectivity. Nature Chemistry 2014, 6, 94-96. http://doi.org/10.1038/nchem.1851

2013

Newcomb, E. T.; Ferreira, E. M. Highly Enantiospecific Platinum-Catalyzed Cycloisomerizations: Synthesis of Enantioenriched Oxabicycloheptene Derivatives. Organic Letters 2013, 15, 1772 - 1775. http://doi.org/10.1021/ol400625f

Barczak, N. T.; Rooke, D. A.; Menard, Z. A.; Ferreira, E. M. Stereoselective Synthesis of Tetrasubstituted Olefins through a Halogen-Induced 1,2-Silyl Migration. Angewandte Chemie International Edition 2013, 52, 7579 - 7582. http://doi.org/10.1002/anie.201303007

Allegretti, P. A.; Ferreira, E. M. Platinum-catalyzed cyclizations viacarbene intermediates: syntheses of complementary positional isomers of isoxazoles. Chem. Sci. 2013, 4, 1053 - 1058. http://doi.org/10.1039/c2sc21671j

Allegretti, P. A.; Ferreira, E. M. Vicinal Bisheterocyclizations of Alkynes via Nucleophilic Interception of a Catalytic Platinum Carbene. Journal of the American Chemical Society 2013, 135, 17266 - 17269. http://doi.org/10.1021/ja408957a

2012

Rooke, D. A.; Ferreira, E. M. Palladium-Catalyzed Hiyama Couplings of α-Silylenoates and α-Silylenamides. Organic Letters 2012, 14, 3328 - 3331. http://doi.org/10.1021/ol301300r

Stache, E. E.; Seizert, C. A.; Ferreira, E. M. Molecular scaffolds with remote directing groups for selective palladium-catalyzed C–H bond functionalizations. Chemical Science 2012, 3, 1623 - 1628. http://doi.org/10.1039/c2sc20176c

Rooke, D. A.; Ferreira, E. M. Platinum-Catalyzed Hydrosilylations of Internal Alkynes: Harnessing Substituent Effects to Achieve High Regioselectivity. Angewandte Chemie International Edition 2012, 51, 3225 - 3230. http://doi.org/10.1002/anie.201108714

2011

Allegretti, P. A.; Ferreira, E. M. Generation of α,β-Unsaturated Platinum Carbenes from Homopropargylic Alcohols: Rearrangements to Polysubstituted Furans. Organic Letters 2011, 13, 5924 - 5927. http://doi.org/10.1021/ol202649j

2010

Rooke, D. A.; Ferreira, E. M. Stereoselective Syntheses of Trisubstituted Olefins via Platinum Catalysis: α-Silylenones with Geometrical Complementarity. Journal of the American Chemical Society 2010, 132, 11926 - 11928. http://doi.org/10.1021/ja1058197