Johnson Group – Professor Product Portal
Professor Jeffrey S. Johnson
The Johnson group has developed a family of reagents that are useful for the modular preparation of highly substituted glycolic acid derivatives. Silyl glyoxylates are potent electrophiles by virtue of being α-dicarbonyls, and react with a variety of nucleophiles. The intermediates generated undergo 1,2-silyl migration followed by electrophilic trapping with aldehydes, enones, nitroolefins, ketones, or lactones to give highly functionalized, fully substituted glycolates.
J.S. Johnson Group Website
Recent papers from the Johnson Group
1.
Boyce GR, Liu S, Johnson JS. 2012. Construction of Cyclopentanol Derivatives via Three-Component Coupling of Silyl Glyoxylates, Acetylides, and Nitroalkenes. Org. Lett.. 14(2):652-655. https://doi.org/10.1021/ol2033527
2.
Boyce GR, Greszler SN, Johnson JS, Linghu X, Malinowski JT, Nicewicz DA, Satterfield AD, Schmitt DC, Steward KM. 2012. Silyl Glyoxylates. Conception and Realization of Flexible Conjunctive Reagents for Multicomponent Coupling. J. Org. Chem.. 77(10):4503-4515. https://doi.org/10.1021/jo300184h
3.
Nicewicz DA, Satterfield AD, Schmitt DC, Johnson JS. 2008. Self-Consistent Synthesis of the Squalene Synthase Inhibitor Zaragozic Acid C via Controlled Oligomerization. J. Am. Chem. Soc.. 130(51):17281-17283. https://doi.org/10.1021/ja808347q
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DISCIPLINES
- Organic Synthetic Chemistry
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