Donald A. Watson, University of Delaware

Donald A. Watson was born in California in 1976. He received his BS in Chemistry from UC San Diego in 1998. During his undergraduate years, he worked in the laboratories of Professors K.C. Nicolaou and Emmanuel Theodorakis, working on natural products synthesis.

He completed his PhD in Organic Chemistry at UC Irvine in 2004, working under the direction of Professor Larry E. Overman. His dissertation work focused on stereochemical problems in palladium catalyzed transformations.

From 2004 to 2006 he was a NIH Postdoctoral Fellow in the laboratories of Professor Robert G. Bergman at UC Berkeley. During this time he developed zirconium-based catalysts for asymmetric intramolecular hydroaminations. He then moved to the Massachusetts Institute of Technology as to take a position as a Postdoctoral Associate in Professor Stephen L. Buchwald's laboratory, where he studied metal catalyzed processes C-F bond formation.

He joined the Chemistry and Biochemistry faculty at the University of Delaware as an Assistant Professor in July 2009.

1. Bimetallic Complexes for Remote Substrate-Directed Catalysis.

2.New Methods for the Preparation of a-Chiral Amines.

3. Electrocatalysts for the Reduction of CO2 to Methanol.

Publications:
pending

Bischler-Napieralski reaction

reagent: pocl3
solvent: mecn, benzene, toluene, dcm, dmpu.
temp: rt - reflux
time: several hours.

not a nice and clean reaction. usually low yielding because of the strong acidic condition.
the product imine is sometimes not stable.

some milder conditions:
1. pph3/ccl4/reflux
2. Tf2O

a nice link:

http://www.organic-chemistry.org/namedreactions/bischler-napieralski-reaction.shtm

Mary Watson, University of Delaware

Mary Waterson,
BS, 2000, Harvard University, phd, 2006 with Larry E. Overman, 2006–2009, postdoc with Eric N. Jacobsen. During her postdoc, she developed a nickel-catalyzed method for olefin arylcyanation via activation of C–CN bonds. She joined the faculty at the University of Delaware in July 2009.
Research:
centered on the discovery of new catalytic, stereoselective methods for organic synthesis by utilizing the power of both transition metal and Brønsted acid catalysts.
1. Selective Activation of Relatively Strong Bonds
C-H activation.
2. Brønsted Acid-Catalyzed Reactions of Unactivated Olefins
enantioselective additions of H–X (X = C, O, N, etc.) across olefins.

publication:
pending

A proposal of synthesis of maoecrystal V

In 2004, islolated was the maoecrystal V with a novel C19 skeleton from the leaves of a Chinese medicinal herb, Isodon eriocalyx. it is remarkably active against HeLa cells (IC50) 0.02 ug/mL).
The two chiral quaternary carbons and a tertiary alcohol in a contiguous setting served to pose interesting challenges to the science of chemical synthesis.
So far, no total synthesis. the following are just my thoughts.











another one. not better.










or umpolung chemistry.(sorry, one methyl is missing in the product).

what can you do if your precious compound spilled?

My precious compound spilled out of a bottle and sticked onto a piece of plastic foam. the foam was dissolved by the dcm which is the solvent with my compound.
Discard it ? no, the boss will kill me.

1 I cut the foam off and dissolved the foam (with my compound) with DCM/EtoAc.
The foam dissolved without problem. concentrated. passed a pad of silica gel, eluting with etoac, nothing can be removed.
2. checked the structure of the foam through internet, it is polystyrene,
http://en.wikipedia.org/wiki/Polystyrene
tried to run a TLC with pure polystyrene, no obvious spots.

3. tested the solubility of the foam in organic solvents.
soluble: dcm, etoac, ether
unsoluable: meoh, hexanes,
4. so meoh was added to precipitate the polystyrene, and a simple filtration with silica gel removed the plastic.

The radical reactions of imine radicals

Tetrahedron
Volume 65, Issue 36, 5 September 2009, Pages 7415-7421

In conclusion, imine radicals 5 and 15 can be generated from the manganese(III), silver(II) oxidation of 2-amino-1,4-benzoquinones. These free radical reactions provide efficient methods for the generation of the dimeric products 4 and 14. In the presence of styrene, twistane 17 was afforded from 2-phenylamino-1,4-benzoquinone 1 via a radical annulation reaction of imine radical 5.

mechanism:

Peptide–Dirhodium Ligation

Controlling Peptide Structure with Coordination Chemistry: Robust and
Reversible Peptide–Dirhodium Ligation
DOI: 10.1002/chem.200901266
Chem. Eur. J. 2009, 00, 0 – 0

interesting paper.