J.S. Johnson Group – Professor Product Portal

Professor Product Portal Index

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

For applicable product information, please click below:

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