Protecting Group Reaction Searching Guide for SciFinder Scholar
Purpose: demonstrate how to
- search SciFinder Scholar by chemical reaction
- specify two functional groups; one reacts and the other doesn't - this is typical of a protecting group
Example: find journal articles to reactions where an actonide-type protecting group is removed from a terminal 1,2 diol in the presence of a primary hydroxyl group which has been protected with any silyl group (RCH2O-Si).
- Open SciFinder Scholar. From in-library computers, use the Search Tools - Find Databases page, and choose SciFinder Scholar[UM Library Terminal Services].
- Click on the Use Scifinder Scholar link. Once it connects, accept the Scholar license terms.
- Choose the Chemical Substance or Reaction explore option.
- Choose the Chemical Structure option.
- Draw each of the reactant groups as shown below. Note that we are allowing for ketals other than just acetone-based (such as 3-pentanone) by not specifiying substitutents on the ketal carbon.

Tip: to easily draw the products, use the lasso tool
to select the reactants, then copy and paste.
Use the eraser and other drawing tools to make the needed changes in the products.
Screen should look something like the following:
Now, use the Reaction Arrow button 
to note which are reactants and which are products.
Note that this only works if you have drawn the reactants on the left and the products on the right.
Otherwise, you may use the reaction roles button
to assign roles.

- Now, use the Atom Mapping button
to indicate that a particular atom in the reactant becomes a particular atom in the product.
- We will use the primary oxygen of the acetonide, and the carbon attached to the silylated oxygen as our mapped atoms.
- Click on the atom-mapping button, then on the reactant atom, and then on the corresponding product atom.
It should look similar to following:

Next, select the Get Reactions button.
Choose the "substructure of more complex structures" option and then select OK.
Following is one of the reaction results that the search found (approximately 87 reactions and 23 literature references as of August 2005).
Note: these results may not include every reported occurence of this transformation in Chemical Abstracts or the literature. This SciFinder Scholar reaction searches only selected reactions from the articles it indexes. For more complete coverage, also try a Beilstein protecting group search - see UM Science Library's Beilstein Protecting Group Reaction Search Guide for details. Where thoroughness is essential, you should also consider a SciFinder Scholar structure/substructure search on the desired product, limit results to preparations, and browse the results.

- It may be of interest to see what catalysts/reagents are most frequently reported. Use the Analyze/Refine button, choose Analyze, and Analyze by Catalyst. In this case, pyridinium tosylate appears to be the most frequently used catalyst. Return to the results page; use the Back button as needed.
- Use the checkboxes to mark reactions of interest and then use the Get References button.
- Please exit (logoff) when finished to free up a slot for a classmate or researcher to use Scholar. There are a very limited number of users allowed for UM's subscription.
- To find a copy of the article listed (which will have more details of the reaction), please use the MGet It Citation Finder or see the Science Library's How to Find a Journal Article guide.
For suggestions or additional chemistry literature research assistance contact David R. Peck (webpage).