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Stereochemistry
Gordon Research Conference

21st Century Stereochemistry: Synthesis, Structure, Function, and Properties

Dates

July 24-29, 2016

Location

Salve Regina University
Newport, RI

Organizers

Chairs:
Scott E. Denmark & John A. Ragan

Vice Chairs:
Gregory C. Fu & Cameron J. Cowden

Meeting Description

Stereochemistry suffuses all aspects of molecular, macromolecular and supramolecular science. In keeping with its unifying purview, the 2016 Gordon Research Conference on Stereochemistry will feature the most recent advances in synthesis, catalysis, structure and function. The most centrist activities of stereoselective synthesis will highlight contributions in the domains of organic and organometallic catalysis, and main group asymmetric synthesis, for the construction of carbon-carbon and carbon heteroatom bonds with extraordinary diversity and stereocontrol. In all of these domains, special emphasis will be placed on detailed mechanistic investigations on the origins of stereoselectivity.

Stereoselective synthesis is of paramount importance in the industrial sector both in pharmaceuticals, sensors, and materials. The impact of stereochemistry will be illustrated in case studies on the discovery of stereochemically complex compounds that provide solutions to the multidimensional problem of therapeutic activity, bioavailability, non-toxicity and metabolic stability. From there, the challenges of synthesizing such materials on commercial production scales in stereocontrolled fashion will be presented for some of the most important life-saving molecules.

Nature, the quintessential stereochemist, has learned to engineer extraordinary stereoselectivity in the synthesis of everything in the biosphere. The mechanisms of enzymatic catalysis of large families of natural products will be a major theme as well as the advances in engineered biocatalysts for production of non-natural target molecules.

The universe of higher order stereochemistry found in polymers, supramolecular structures, and materials provides extraordinary opportunities for exquisite design of function from exquisite control of structure. Programmed polymers, sensors, devices, and molecular machines all require precise control of shape and directionality that emerge as function. The 2016 GRC will bring together world experts in these fields to interact with world experts in the molecular sciences to stimulate exchange of ideas that can advance both disciplines. The fresh insights that emerge from novel perspectives can often initiate new areas of inquiry.

The 2016 conference will include 29 speakers divided into nine sessions. There will also be four poster sessions for attendees to share their most recent, often unpublished results, and informal discussions will be fostered during the afternoons and after the evening lectures.

Contributors

Final Meeting Program

Sunday
2:00 pm - 9:00 pmArrival and Check-in
6:00 pmDinner
7:30 pm - 7:40 pmWelcome / Introductory Comments by GRC Site Staff
7:40 pm - 9:30 pmFrontiers of Stereochemistry: Synthesis and Mechanism
Discussion Leader: Gregory Fu (California Institute of Technology, USA)
7:40 pm - 8:25 pmDonna Blackmond (The Scripps Research Institute, USA)
"Stereochemical Considerations in Prebiotic Chemistry"
8:25 pm - 8:35 pmDiscussion
8:35 pm - 9:20 pmDavid MacMillan (Princeton University, USA)
"New Photoredox Reactions"
9:20 pm - 9:30 pmDiscussion
Monday
7:30 am - 8:30 amBreakfast
9:00 am - 12:30 pmStereoselective Organocatalysis
Discussion Leader: Noah Burns (Stanford University, USA)
9:00 am - 9:35 amBenjamin List (Max Planck Institute for Coal Research, Germany)
"A New Approach to Asymmetric Lewis Acid Catalysis"
9:35 am - 9:45 amDiscussion
9:45 am - 10:20 amBabak Borhan (Michigan State University, USA)
"Mechanistic Interrogations of Olefin Chlorofunctionalization"
10:20 am - 10:30 amDiscussion
10:30 am - 11:00 amCoffee Break
11:00 am - 11:35 amHelma Wennemers (ETH Zurich, Switzerland)
"Bioinspired Asymmetric Catalysis"
11:35 am - 11:45 amDiscussion
11:45 am - 12:20 pmDean Toste (University of California, Berkeley, USA)
"Concepts and Catalysts for Anion-Controlled Enantioselective Catalysis"
12:20 pm - 12:30 pmDiscussion
12:30 pmLunch
1:30 pm - 4:00 pmFree Time
4:00 pm - 6:00 pmPoster Session
6:00 pmDinner
7:30 pm - 9:30 pmBiosynthesis and Biocatalysis
Discussion Leader: Rajesh Kumar (Pfizer Worldwide Research & Development, USA)
7:30 pm - 8:00 pmGeert-Jan Boons (University of Georgia, USA)
"Carbohydrate Complexity and Molecular Recognition"
8:00 pm - 8:05 pmDiscussion
8:05 pm - 8:35 pmNicholas Turner (University of Manchester, United Kingdom)
"Discovery of a Multi-Functional Biocatalyst for Chiral Amine Synthesis"
8:35 pm - 8:40 pmDiscussion
8:40 pm - 9:20 pmDavid Cane (Brown University, USA)
"Nature as Stereochemist"
9:20 pm - 9:30 pmDiscussion
Tuesday
7:30 am - 8:30 amBreakfast
8:30 amGroup Photo
9:00 am - 12:30 pmStereoselective Synthesis in Industry
Discussion Leader: Francis Gosselin (Genentech, Inc., USA)
9:00 am - 9:35 amCarl Busacca (Boehringer-Ingelheim Pharmaceuticals, Inc., USA)
"Hydrophosphinations of Spring-Loaded Cyclobutanes: Access to Novel Phosphine Reagents"
9:35 am - 9:45 amDiscussion
9:45 am - 10:20 amFrancisco Gonzalez-Bobes (Bristol-Myers Squibb, USA)
"Process Research and Development for the Synthesis of a Pharmaceutical Candidate"
10:20 am - 10:30 amDiscussion
10:30 am - 11:00 amCoffee Break
11:00 am - 11:35 amLaurie Schenkel (Amgen, USA)
"Discovery and Synthesis of AM-6138: A Potent and Selective Inhibitor of β-Secretase Featuring a Novel Warhead"
11:35 am - 11:45 amDiscussion
11:45 am - 12:20 pmBob Scott (Gilead Sciences, USA)
"Development of a Dynamic Resolution Strategy to Synthesize the Chiral Phosphonamidate of GS-7340"
12:20 pm - 12:30 pmDiscussion
12:30 pmLunch
1:30 pm - 4:00 pmFree Time
4:00 pm - 6:00 pmPoster Session
6:00 pmDinner
7:30 pm - 9:30 pmPhysical Methods of Stereochemistry
Discussion Leader: Corinna Schindler (University of Michigan, USA)
7:30 pm - 8:00 pmJoel Hawkins (Pfizer, USA)
"Sequential One-Pot Additions of a Magnesium Ate Complex and an Amine to a 1,4-Ketoester Followed by Carbonyl-Directed Fluoride Addition for the Scalable Synthesis of an H3 Antagonist"
8:00 pm - 8:05 pmDiscussion
8:05 pm - 8:35 pmLeo Joyce (Merck & Co., USA)
"Circular Dichroism Spectroscopy: A Powerful Tool for Complex Stereochemical Analysis"
8:35 pm - 8:40 pmDiscussion
8:40 pm - 9:20 pmDean Tantillo (University of California, Davis, USA)
"Non-Traditional Stereocontrol Elements"
9:20 pm - 9:30 pmDiscussion
Wednesday
7:30 am - 8:30 amBreakfast
9:00 am - 12:30 pmHigher Order Stereochemistry: Beyond the Molecule
Discussion Leader: Brett Fors (Cornell University, USA)
9:00 am - 9:35 amEgbert Meijer (Eindhoven University of Technology, The Netherlands)
"Consequences of Chirality on the Pathway Selection in Supramolecular Systems"
9:35 am - 9:45 amDiscussion
9:45 am - 10:20 amLia Addadi (Weizmann Institute of Science, Israel)
"On Cholesterol Crystallization: From Lipid Bilayer Membranes to Atherosclerosis"
10:20 am - 10:30 amDiscussion
10:30 am - 11:00 amCoffee Break
11:00 am - 11:35 amKaren Wooley (Texas A&M University, USA)
"Expanding the Scopes of Synthetic Organic and Polymer Chemistries: Utilization of the Inherent Stereochemical and Functional Diversities of Natural Products to Produce Unique Materials"
11:35 am - 11:45 amDiscussion
11:45 am - 12:20 pmFraser Stoddart (Northwestern University, USA)
"The Stereochemistry of the Mechanical Bond"
12:20 pm - 12:30 pmDiscussion
12:30 pmLunch
1:30 pm - 4:00 pmFree Time
4:00 pm - 6:00 pmPoster Session
6:00 pmDinner
7:00 pm - 7:30 pmBusiness Meeting
Nominations for the Next Vice Chair; Fill in Conference Evaluation Forms; Discuss Future Site and Scheduling Preferences; Election of the Next Vice Chair
7:30 pm - 9:30 pmStereoselective Synthesis
Discussion Leader: Thomas Maimone (University of California, Berkeley, USA)
7:30 pm - 8:00 pmRobert Knowles (Princeton University, USA)
"Proton-Coupled Electron Transfer in Organic Synthesis and Asymmetric Catalysis"
8:00 pm - 8:05 pmDiscussion
8:05 pm - 8:35 pmJennifer Schomaker (University of Wisconsin-Madison, USA)
"Catalyst-Controlled, Flexible Strategies for the Synthesis of Complex Amines"
8:35 pm - 8:40 pmDiscussion
8:40 pm - 9:20 pmVarinder Aggarwal (Bristol University, United Kingdom)
"Assembly Line Synthesis"
9:20 pm - 9:30 pmDiscussion
Thursday
7:30 am - 8:30 amBreakfast
9:00 am - 12:30 pmStereoselective Organometallic Catalysis
Discussion Leader: David Sarlah (University of Illinois at Urbana-Champaign, USA)
9:00 am - 9:35 amPeter Zhang (Boston College, USA)
"Metalloradical Catalysis for Stereoselective Radical Reactions"
9:35 am - 9:45 amDiscussion
9:45 am - 10:20 amRobert Bergman (University of California, Berkeley, USA)
"Chemical and Stereochemical Modification of Reactions Caused by Encapsulation of Substrates in Water-Soluble Supramolecular Systems"
10:20 am - 10:30 amDiscussion
10:30 am - 10:45 amCoffee Break
10:45 am - 11:20 amJohn Hartwig (University of California, Berkeley, USA)
"Approaches to Asymmetric Functionalization with Artificial Metalloenzymes"
11:20 am - 11:30 amDiscussion
11:30 am - 11:45 amSelected from Poster Abstracts: Takahiko Akiyama (Gakushuin University, Japan)
"Enantioselective Synthesis of Chiral Biaryls by Means of Chiral Phosphoric Acid"
11:45 am - 11:50 amDiscussion
11:50 am - 12:05 pmSelected from Poster Abstracts: Scott Rychnovsky (UC Irvine, USA)
"Assigning Configuration Using the Competing Enantioselective Conversion (CEC) Strategy"
12:05 pm - 12:10 pmDiscussion
12:10 pm - 12:25 pmSelected from Poster Abstracts: Corey Stephenson (University of Michigan, USA)
"Synthesis of Resveratrol Tetramers via a Stereoconvergent Radical Equilibrium"
12:25 pm - 12:30 pmDiscussion
12:30 pmLunch
1:30 pm - 4:00 pmFree Time
4:00 pm - 6:00 pmPoster Session
6:00 pmDinner
7:30 pm - 9:30 pmKeynote Session: Structure and Function
Discussion Leader: Cameron Cowden (Concert Pharmaceuticals, USA)
7:30 pm - 8:15 pmAmir Hoveyda (Boston College, USA)
"Stereoselective Catalysis as a Tool for Study of Mechanism"
8:15 pm - 8:25 pmDiscussion
8:25 pm - 9:10 pmDieter Seebach (ETH Zurich, Switzerland)
"From Synthetic Methodology to Biophysics"
9:10 pm - 9:20 pmDiscussion
9:20 pm - 9:30 pmClosing Remarks
Friday
7:30 am - 8:30 amBreakfast
9:00 amDeparture
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