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CEOverture...
This newsletter is dedicated to previewing the upcoming National ACS Meeting in San Francisco. As the long list of fluorous-related posters and presentations below shows, fluorous chemistry continues to deepen and broaden its technological reach. The meeting would be a fine time to chat about opportunities to apply fluorous techniques in your research. I hope to see you there and have the chance to meet!
Cheers,
Phil
Philip E. Yeske
President & CEO
Fluorous Presence at the ACS Meeting
The 232nd ACS Meeting will be held in San Francisco September 10-14, 2006. Topics in fluorous chemistry that will be covered include the latest developments in small molecule, carbohydrate synthesis, catalysis, natural product synthesis and combinatorial chemistry. Scientists representing a number of disciplines will present their latest research. Oral papers and Poster Presentations utilizing Fluorous Chemistry are summarized below with the time and location of each presentation cited. The abstract of each of these presentations can also be found at http://oasys2.confex.com/acs/232nm/techprogram/ .
Are you new to fluorous chemistry and want to learn more? Visit us at the FTI Poster Presentation on Sunday evening to learn more about what Fluorous Technologies has to offer and how fluorous chemistry can help improve your productivity. If you prefer, drop us a note to arrange a meeting with FTI staff to discuss synthesis or separation problems that you are encountering that could possibly be solved through the use of fluorous chemistry.
Are you a current FTI customer? Stop by and share your success stories with us! We are always interested to hear how our customers are using our products.
"Fluorous" Presentations
ORGANOCATALYSIS
Title: ORGN 21 – “(S)-Pyrrolidine sulfonamide and its recyclable version for promoting
enantioselective organic reactions in organic and aqueous media”
Author: Jian Wang, Hao Li, Liansuo Zu, and Wei Wang. University of New Mexico
Date/Place: Sept 10, 8:20AM – Moscone Center, Room 131
BIPHASIC CATALYSIS
Title: FLUO 9 – “Synthesis, structure and reactivity of dichloro-palladium(II) 2,2'-bipyridine
complex with perfluorooctyl 4,4'-O-alkylated ponytail [(C8F17CH2OCH2-C5H3N)2]”
Author: Norman Lu, Jeng-Yung Chen, Chi-Wen Fan, and Yuan-Chow Lin. National Taipei University of Technology
Date/Place: Sept 10, 4:25PM – San Francisco Marriott, Salon 5
Title: MEDI 67 – “Fluorous-phase synthesis of minor groove binding agents related to distamycin”
Author: Steven M. Firestine, Wayne State University
Date:/Place: Sept 10, 7:00-9:00PM – Moscone Center, Hall D-Poster
Title: ORGN 234 – “Diversity-oriented synthesis of novel heterocyclic libraries by fluorous
synthesis”
Author: Wei Zhang, Yimin Lu, and Christine H-T. Chen. Fluorous Technologies, Inc.
Date/Place: Sept 10, 8:00-10:00PM – Moscone Center, Hall D-Poster
Title: ORGN 149 – “A recyclable fluorous (S)-pyrrolidine sulfonamide-promoted direct, highly
enantioselective Michael addition ketones and aldehydes to nitroolefins in water”
Author: Liansuo Zu, Jian Wang, Hao Li, and Wei Wang. University of New Mexico.
Date/Place: Sept 10, 8:00-10:00PM – Moscone Center, Hall D-Poster and Sept 11, 8:00-10:00PM – Moscone Center, Hall D-Sci-Mix
NATURAL PRODUCT SYNTHESIS
Title: ORGN 289 – “Synthesis of dictyostatin and analogs by traditional and fluorous methods”
Author: Dennis Curran, University of Pittsburgh.
Date/Place: Sept 11, 2:00PM – Moscone Center, Room 134
Title: CHED 323 – “Synthesis of a recyclable fluorous Rh(II) catalyst for carbenoid insertion
reactions”
Author: Joel A. Newmiller, Rachel E. Ozick, Rebecca S. Slogic, and Allen M. Schoffstall. University of Colorado at Colorado Springs.
Date/Place: Sept 11, 2:30-4:30PM – Moscone Center, Hall D-Poster
CARBOHYDRATE SYNTHESIS
Title: CARB 28 – “Carbohydrate microarrays and automated fluorous-phase oligosaccharide
synthesis”
Author: Nicola L. Pohl, Iowa State University.
Date/Place: Sept 11, 3:20PM – Hilton San Francisco, Yosemite C
Title: ORGN 540 – “Fluorous phase Pummerer cyclative-capture for the synthesis of N-
heterocycles”
Author: David J. Procter, Rosemary A. McCormick , Laura A. McAllister , and Karen M. James. The University of Manchester.
Date/Place: Sept 12, 8:00-10:00PM – Moscone Center, Hall D-Poster
HIGH-THROUGHPUT ORGANIC SYNTHESIS
Title: ORGN 624 – “High-throughput organic synthesis using fluorous technology”
Author: Yimin Lu, Tadamichi Nagashima, and Wei Zhang . Fluorous Technologies, Inc.
Date/Place: Sept 13, 11:30AM – Moscone Center, Room 135
Title: MEDI 546 – “Novel synthesis of heterocyclic fluorous b-amino acids using a multifunctional
scaffold”
Author: Xiaobing Wang Sr. and Kit S. Lam. University of California, Davis
Date/Place: Sept 13, 7:00-9:00PM – Moscone Center, Hall D-Poster
COMBICHEM
Title: ORGN 898 – “New development of fluorous separation techniques for parallel and high-
throughput synthesis”
Author: Wei Zhang, Fluorous Technologies Inc.
Date/Place: Sept 14, 8:00AM – Moscone Center, Room 132
NATURAL PRODUCT SYNTHESIS
Title: ORGN 918 – “Progress toward the total synthesis of psymberin toward the total synthesis of
psymberin”
Author: James R. Davies, Yakira R. Landaverry, Sandra Ast, Kirsten Milinkevich, Brian S. Gerstenberger, and Joseph P. Konopelski. University of California Santa Cruz
Date/Place: Sept 14, 3:40PM – Moscone Center, Room 134
Here is additional background on a couple of the presentations listed above:
Automated Fluorous-phase Carbohydrate Synthesis
The Pohl group at Iowa State University reported the first example to immobilize carbohydrates for microarray using fluorous techniques. This talk will provide an overview of an exciting new approach to carbohydrate synthesis that is under development together with FTI.
CARB 28 - “Carbohydrate microarrays and automated fluorous-phase oligosaccharide synthesis”
Nicola L. Pohl, Iowa State University
An understanding of immune responses to carbohydrates is vital for rational vaccine design, but is currently limited in part because well-defined saccharide structures are difficult to access. This talk will discuss automated fluorous-phase carbohydrate synthesis as an alternative to solid-phase approaches for the rapid synthesis of oligosaccharides and how this fluorous-tagging strategy also facilitates methods for directly screening these synthetic carbohydrates for their biological activities
Image courtesy of Nicola Pohl, Iowa State University
References:
1. Ko, K.-S.; Jaipuri, F. A.; Pohl, N. L. J. Am. Chem. Soc. 2005, 127, 13162-13163.
2. Mamidyala, S. K.; Ko, K.-S.; Jaipuri, F. A.; Park, G.; Pohl, N. L. J. F. Chem. 2006, 127, 571-579.
Fluorous Organocatalyst for Enantioselective Michael Addition Reactions
Researchers from the University of New Mexico will be presenting both a poster and an oral presentation on the development of a new organocatalyst for use in enantioselective Michael addition reactions.
ORGN 149 – “A recyclable fluorous (S)-pyrrolidine sulfonamide-promoted direct, highly
enantioselective Michael addition ketones and aldehydes to nitroolefins in water”
Liansuo Zu, Jian Wang, Hao Li, and Wei Wang. Department of Chemistry, University of New Mexico
ORGN 21 – “(S)-Pyrrolidine sulfonamide and its recyclable version for promoting enantioselective
organic reactions in organic and aqueous media”
Jian Wang, Hao Li, Liansuo Zu, and Wei Wang. University of New Mexico
A recyclable and reusable fluorous (S)-pyrrolidine sulfonamide organocatalyst has been developed for promoting highly enantio- and diastereoselective Michael addition reactions of ketones and aldehydes with nitroolefins in water. The organocatalyst is conveniently recovered from the reaction mixtures by fluorous solid-phase extraction and can be subsequently reused (up to 6 cycles) without a significant loss of catalytic activity and stereoselectivity.
References:
1. Zu, L.; Wang, J.; Li, H.; Wang, W. Org Lett. 2006, 8, 3077-3079.
2. Zu, L.; Wang, J.; Li, H.; Yu, X.; Wang, W. Tetrahedron Lett. 2006, 47, 5131-5134.
FTI Open Forum: Your Questions Answered
From time-to-time we have been publishing frequently asked questions regarding fluorous chemistry. One question that we are often asked when users are new to fluorous chemistry appears below.
Question: I routinely synthesize small molecules and peptides. Do I need to use fluorous solvents in the synthesis of my compound when utilizing fluorous tags or reagents? What are the best solvents to use?
FTI Scientist, Dr. Tadamichi Nagashima offers this answer:
“Most fluorous compounds that have one C8F17 or two C6F13 groups (light fluorous) retain the solubility properties of their organic counterpart very well; so in most cases, the solvent system that is used with the organic material can be used for your fluorous reactions. For example, Mitsunobu reactions with F26-DIAD and F17-triphenylphosphine can be run in THF. After quick aqueous workup, the excess reagents and their by-products can be quickly removed by F-SPE. In general, you can utilize any organic solvent for reactions involving light fluorous materials.
On the other hand, reagents that have three or more C8F17 groups (heavy fluorous) tend to have poor solubility in most organic solvents. Typically, THF is the first solvent to try when attempting to dissolve heavy fluorous compounds. If THF doesn’t work, then addition of a fluorous-organic hybrid solvent such as HFE-7100 (perfluorobutyl methyl ether) typically solves the solubility problems.”
We appreciate and continue to seek the input of our colleagues and welcome you, our reader, to submit ideas for future newsletters. This newsletter is our vehicle to provide our customers with the most current developments happening both at Fluorous Technologies and in the fluorous chemistry research community. Is there a specific topic that you would like to see us cover? Do you have a paper that you recently published that you would like to see reviewed? Is there a presentation for which you would like a wider audience? Email them to us. We will personally reply to all comments and questions received in a timely manner and publish as many as we can.