Gregory Dake

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Gregory Dake

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Research and Teaching Interests

My research program is directed towards the creation, understanding and application of methods within organic synthesis.

Catalysis. Our group has a long-standing interest in catalysis within synthetic organic chemistry. Students interested in catalysis and synthesis have the opportunity to work within the CREATE Sustainable Synthesis Industrial program.
For example:
• CREATE Sustainable Synthesis: the construction of medicinally relevant heterocycles using transition metal catalysis
• Ligand Design: collaboratively with Professor Derek Gates, we have designed a set of chiral, phosphaalkene (two-coordinate P) ligands (PhAk-Ox, PhAk-phen-Ox, PhAk-pyr-Ox) for use in catalysis and macromolecular chemistry.
• DMAP catalyzed cyclizations to form tetrahydroxanthones
• Metal Catalyzed Annulation: Pt(II), Ag(I), Au(I) catalyzed cyclizations onto alkynes. High yielding, mild, multibond forming processes to form complex heterocycles.

Molecule Synthesis. We are always interested in the total synthesis of natural products and natural product-like molecular structures. Examples: cladionamides, fawcettidine, nitiol, fasicularin
• Function Oriented Synthesis: at times it may be appropriate to construct simpler analogs of natural products to examine bioactive mechanisms and/or medicinal chemistry. Projects such as this are typically collaborative with other researchers.
Students trained in synthetic organic chemistry think deeply about the relationships between molecular structure, chemical reactivity and reaction mechanism. Thus, they are typically well poised to pursue a number of avenues of scientific inquiry in academia and industry later in their careers.
...........

About Gregory Dake: Gregory Dake was a B.Sc. (Hons) student at UBC a long time ago. He did undergraduate research with Professor Raymond Andersen. He then earned his Ph.D. at Stanford University with Professor Barry Trost, working on reactions catalyzed by ruthenium(II) complexes and nucleophilic phosphines.  Postdoctoral work with Gilbert Stork at Columbia University (in the City of New York) on the total synthesis of quinine followed. Employment at UBC followed. He was awarded a Science Undergraduate Society Teaching Excellence award in 2010 and a UBC Killam Teaching Prize in 2012. He believes in the concept of deliberate practice in education. He was a UBC Sustainability Initiative Teaching and Learning Fellow in 2013. Currently is the Associate Head-Undergraduate Affairs in the Department of Chemistry. When he commutes, he often listens to the following podcasts: Doughboys, You Must Remember This, 99% Invisible, Switched on Pop, Pistol Shrimps Radio, The Axe Files, Frontline, Football Weekly with James Richardson, Rosenthal and Jeselnik Podcast (rjvp!), Men in Blazers, Freakonomics, Never Not Funny, The Secret History of Hollywood.

Contact

Real name: 
Email: 
Office Room Number(s): 
Chem A341
Office Phone Number: 
604-822-9121
Fax Number: 
604-822-2847

Curriculum Vitae

B.Sc.(Hons.), British Columbia (1992); Ph.D. Stanford University (Barry M. Trost, 1998); Postdoctoral, Columbia University (Gilbert Stork, 1998-1999).

2010 Science Undergraduate Society Teaching Excellence Award

2012 University of British Columbia Killam Teaching Prize

2013 University of BC Sustainability Teaching and Learning Fellow

2016 Associate Head, Undergraduate Affairs

Publications

2016

Serin, S. C. ; Dake, G. R. ; Gates, D. P. Phosphaalkene-Oxazoline Copolymers With Styrene As Chiral Ligands For Rhodium(I). Dalton Transactions 2016, 45, 5666.
Serin, S. C. ; Dake, G. R. ; Gates, D. P. Copper(I) Complexes Of Pyridine-Bridged Phosphaalkene-Oxazoline Pincer Ligands. Inorganic Chemistry 2016, 55, 6678.

2014

Castillo-Contreras, E. B. ; Stahl, A. M. ; Dake, G. R. Annulated Isoxazoles Via [3+2] Cycloaddition Of Alkenyl Bromides And Oximoyl Chlorides And Ag(I) Promoted Elimination. JOURNAL OF ORGANIC CHEMISTRY 2014, 79, 7250-7255.
Castillo-Contreras, E. B. ; Dake, G. R. Dmap Promoted Tandem Addition Reactions Forming Substituted Tetrahydroxanthones. ORGANIC LETTERS 2014, 16, 1642-1645.

2013

Vilin, Y. Y. ; Nunez, J. - J. ; Kim, R. Y. ; Dake, G. R. ; Kurata, H. T. Paradoxical Activation Of An Inwardly Rectifying Potassium Channel Mutant By Spermine: ``(B)Locking'' Open The Bundle Crossing Gate. MOLECULAR PHARMACOLOGY 2013, 84, 572-581.
Sala-Rabanal, M. ; Li, D. C. ; Dake, G. R. ; Kurata, H. T. ; Inyushin, M. ; Skatchkov, S. N. ; Nichols, C. G. Polyamine Transport By The Polyspecific Organic Cation Transporters Oct1, Oct2, And Oct3. MOLECULAR PHARMACEUTICS 2013, 10, 1450-1458.
Loosley, B. C. ; Andersen, R. J. ; Dake, G. R. Total Synthesis Of Cladoniamide G. ORGANIC LETTERS 2013, 15, 1152-1154.

2012

Dugal-Tessier, J. ; Serin, S. C. ; Castillo-Contreras, E. B. ; Conrad, E. D. ; Dake, G. R. ; Gates, D. P. Enantiomerically Pure Phosphaalkene-Oxazolines (Phak-Ox): Synthesis, Scope And Copolymerization With Styrene. CHEMISTRY-A EUROPEAN JOURNAL 2012, 18, 6349-6359.

2010

Dugal-Tessier, J. ; Dake, G. R. ; Gates, D. P. Chiral Phosphaalkene-Oxazoline Ligands For The Palladium-Catalyzed Asymmetric Allylic Alkylation. Organic Letters 2010, 12, 4667 - 4669.
Kozak, J. A. ; Patrick, B. O. ; Dake, G. R. Gold(I)-Catalyzed Intramolecular Tandem Addition/friedel-Crafts Reactions Between Acyclic Enamides And 1-Arylalkynes. Journal of Organic Chemistry 2010, 75, 8585 - 8590.
Dugal-Tessier, J. ; Kuhn, P. - S. ; Dake, G. R. ; Gates, D. P. Synthesis Of Functional Phosphines With Ortho-Substituted Aryl Groups: 2-Rc6H4Ph2 And 2-Rc6H4P(Sime3)2 (R = 2-I-Pr- Or 2-T-Bu-). Heteroatom Chemistry 2010, 21, 265 - 270.

2009

Kozak, J. A. ; Dodd, J. M. ; Harrison, T. J. ; Jardine, K. J. ; Patrick, B. O. ; Dake, G. R. Enamides And Enesulfonamides As Nucleophiles: Formation Of Complex Ring Systems Through A Platinum(Ii)-Catalyzed Addition/friedel-Crafts Pathway. Journal of Organic Chemistry 2009, 74, 6929-6935.

2008

Dake, G. R. ; Fenster, E. E. ; Patrick, B. O. A Synthetic Approach To The Fusicoccane A-B Ring Fragment Based On A Pauson-Khand Cycloaddition/norrish Type 1 Fragmentation. Journal of Organic Chemistry 2008, 73, 6711-6715.
Dugal-Tessier, J. ; Dake, G. R. ; Gates, D. P. Chiral Ligand Design: A Bidentate Ligand Incorporating An Acyclic Phosphaalkene. Angewandte Chemie-International Edition 2008, 47, 8064-8067.
Kozak, J. A. ; Dake, G. R. Total Synthesis Of (+)-Fawcettidine. Angewandte Chemie-International Edition 2008, 47, 4221-4223.

2007

Dugal-Tessier, J. ; Dake, G. R. ; Gates, D. P. P,n-Chelate Complexes Of Pd(Ii) And Pt(Ii) Based On A Phosphaalkene Motif: A Catalyst For The Overman-Claisen Rearrangement. Organometallics 2007, 26, 6481-6486.

2006

Wilson, M. S. ; Woo, J. C. S. ; Dake, G. R. A Synthetic Approach Toward Nitiol: Construction Of Two 1,22-Dihydroxynitianes. Journal of Organic Chemistry 2006, 71, 4237-4245.
Harrison, T. J. ; Kozak, J. A. ; Corbella-Pane, M. ; Dake, G. R. Pyrrole Synthesis Catalyzed By Agotf Or Cationic Au(I) Complexes. Journal of Organic Chemistry 2006, 71, 4525-4529.

2005

Fenster, M. D. B. ; Dake, G. R. An Asymmetric Formal Synthesis Of Fasicularin. Chemistry-a European Journal 2005, 11, 639-649.

2004

Easton, L. P. ; Dake, G. R. Nucleophilic Additions Of Lactam-Derived Enol Triflates To Aldehydes Mediated By Nickel(Ii) And Chromium(Ii) Salts. Canadian Journal of Chemistry-Revue Canadienne De Chimie 2004, 82, 139-144.
Woo, J. C. S. ; Fenster, E. ; Dake, G. R. A Convenient Method For The Conversion Of Hindered Carboxylic Acids To N-Methoxy-N-Methyl (Weinreb) Amides. Journal of Organic Chemistry 2004, 69, 8984-8986.
Dake, G. R. ; Fenster, M. D. B. ; Fleury, M. ; Patrick, B. O. Investigations Of Alpha-Siloxy-Epoxide Ring Expansions Forming 1-Azaspirocyclic Ketones. Journal of Organic Chemistry 2004, 69, 5676-5683.
Dake, G. R. ; Fenster, M. D. B. ; Hurley, P. B. ; Patrick, B. O. Synthesis Of Functionalized 1-Azaspirocyclic Cyclopentanones Using Bronsted Acid Or N-Bromosuccinimide Promoted Ring Expansions. Journal of Organic Chemistry 2004, 69, 5668-5675.

2003

Fenster, M. D. B. ; Dake, G. R. A Formal Construction Of Fasicularin. Organic Letters 2003, 5, 4313-4316.

2001

Fenster, M. D. B. ; Patrick, B. O. ; Dake, G. R. Construction Of Azaspirocyclic Ketones Through Alpha-Hydroxyiminium Ion Or Alpha-Siloxy Epoxide Semipinacol Rearrangements. Organic Letters 2001, 3, 2109-2112.