Grant Detail
This is a chronological listing of grants held by this department, with the most recent listed first. New grants appear in this list weekly and contribute related to the department's Research Profile. The source of grants for this application comes directly from your institution.
Use of Silyl Glyoxylates in Tandem Vinylation/Brook Rearrangement/Aldol Reaction
Johnson Jeffrey
7/1/2007 - 5/11/2008| Sponsoring Organization: | NIH National Institute of General Medical Sciences (NIGMS) |
| Awarding Organization Is: | University of North Carolina at Chapel Hill |
| Project Funding History: | |
| 1/1/1900: | $ 26,676.00 |
| Total: | $ 26,676.00 |
Abstract
Tandem reactions and multicomponent couplings have long been a desirable goal for organic synthesis, as they quickly and efficiently fashion complex molecules from simpler starting materials.1 The long term goal of this project is to devise diastereo- and enantioselective reactions that can be used in the synthetic design of natural products and pharmaceutically relevant building blocks. This proposal focuses on the generation of a,ß-dihydroxy, ?-chiral carbonyl compounds from the domino reaction of silylglyoxylates, vinyl Grignard, and aldehydes. Specifically the strategy presented is to: i) examine induction of enantioselectivity by making a chiral silyl glyoxylate via the ester functionality such as usage of 8-phenyl-menthol, valinol, and phenylalaninol; ii) examine induction of enantioselectivity via chiral Grignard ligands such as (-)-sparteine, trans-1,2-diaminocyclohexane, and N,N-dimethylpseudoephedrine. iii) assess the potential for addition to prochiral aldehydes (e.g. tiglic aldehyde) followed by enantioselective hydroxyl-directed hydrogenation using cationic rhodium or iridium species; iv) utilize the aforementioned methodology in the most concise synthesis to date of the antifungal, phytotoxic natural product alternaric acid.
