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J.S. Johnson Group – Professor Product Portal

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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

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For recent articles from the Johnson Laboratory

Products available at Aldrich from the J.S. Johnson laboratory

     

Gregory R Boyce, Shubin Liu, Jeffrey S Johnson
Organic Letters 2012-01-20
The three-component coupling of Mg acetylides, silyl glyoxylates, and nitroalkenes results in a highly diastereoselective Kuwajima-Reich/vinylogous Michael cascade that provides tetrasubstituted silyloxyallene products. The regio- and diastereoselectivity were studied using DFT calculations. These silyloxyallenes were converted ...Read More
Gregory R Boyce, Stephen N Greszler, Jeffrey S Johnson, Xin Linghu, Justin T Malinowski, David A Nicewicz, Andrew D Satterfield, Daniel C Schmitt, Kimberly M Steward
Journal of Organic Chemistry 2012-05-18
This Perspective describes the discovery and development of silyl glyoxylates, a new family of conjunctive reagents for use in multicomponent coupling reactions. The selection of the nucleophilic and electrophilic components determines whether the silyl glyoxylate reagent will function as a synthetic equivalent to the dipolar gl...Read More
David A Nicewicz, Andrew D Satterfield, Daniel C Schmitt, Jeffrey S Johnson
Journal of the American Chemical Society 2008-12-24
Despite the prevalence of repeating subunits in chiral natural products, stereocontrolled oligomerization is a largely unexplored strategy for construction of carbon skeletal frameworks. This report describes the use of silyl glyoxylates as dipolar glycolic acid synthons in a controlled oligomerization reaction for the efficient...Read More