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PLEASE HELP! - Chemistry Question

Posted : 5/8/2008 10:23:01 PM

Hi, sorry this is a random question, but it's finals week here. Our Organic Chemistry Professor gave us an online portion of our final to do at our own leisure; we can looks for answers anywhere and from anyone, expect from him ("he wants to see how much he taught us" [because that really makes sense Confused ] and therefore we are not allowed to ask him for help until after we turn it in...

The question:

"A protecting group that has a chiral center can be quite the double edged sword. It can be a helpful thing, or a bad thing. Why would it be so?"

So far I have looked through 3 text books, my notes, a lab mannuel, online sources (performed experiments, search engines, etc), and asked every person I know of with a chemistry background (including lower-level Chem Professors here on campus) and cannot find anything pertaining to this question!

so anyone good in Organic Chem? - Please help

janet_rose

Posted : 5/9/2008 7:00:27 AM

Equest94
"A protecting group that has a chiral center can be quite the double edged sword. It can be a helpful thing, or a bad thing. Why would it be so?"

I am not good in Organic Chem, but I did a Google search (blue phrase) and came up with the following sites.

http://www.wipo.int/pctdb/en/wo.jsp?wo=2001002417&IA=WO2001002417&DISPLAY=DESC

"Since the styrene protecting group has a chiral center, the compound 5 is obtained as mixture of 2 diastereomers. However, there is no need to separate the diastereomers because they become one compound in the following deprotection step of styrene protecting group to get compound 12."

http://linkinghub.elsevier.com/retrieve/pii/S0040403905022148

"It is worth noting that the protecting group has a chiral center and is in the racemic form. Therefore, in the protection of a boronic acid with an existing ... "

You would have to pay to read that second article. Googling on the phrase is blue produced the second quote, but I didn't find that phrase on that web page (didn't buy the article)..

Equest94

Posted : 5/9/2008 10:47:24 AM

Ah! Thank you so much. At this point I would take anything. I really appreciate it.

janet_rose

Posted : 5/9/2008 11:51:56 AM

When you verify the correct answer, please post it (in terms as simple as you can LOL). Now I am curious!

janet_rose

Posted : 5/9/2008 12:06:48 PM

Also try googling on protecting group contains a chiral center. You will pull up a number of sites including Chiral Separations: A Tutorial (http://www.cosmoscience.org/Presentations_2006/Chiral_Aurigemma.ppt).

Equest94

Posted : 5/9/2008 12:33:41 PM

Thank you. We probably won't know the answers for a while, but once we find out I will let you know. Smile