Practice problem for final: Idenitfy the Reagents?

[Crazy_Peach]

I really need help on figure out 15-20. Thanks for helping.

[Kaeroll]

For 15,16,17 look up the Sharpless asymmetric dihydroxylation. Not sure about 18 through 20 at this hour of the morning (not had my coffee yet...) but look up asymmetric hydrogenation methods for 18.

[Horza2002]

I think that 17 uses the dihydroylation using osmium tetroxide.

 

18 will be a hydrogenation using D2 Lindlars catalyst to get the cis deterium

 

Not sure about 19

 

20 will be using LiAlD4 as the reagent

[cpncoop]

I'm not sure what the goal of this forum is... If you are in school, I'm hesitant to just give you the answers to these... But if you're looking for resources of where to find them I'd look at:

 

1. LaRocke, Comprehensive Organic Tranformations

 

2. March, Advanced Organic Chemistry

 

3. SciFinder (subscription based)

 

Most colleges will have the first 2, and access to the third. All the answers are there... Good luck.

 

PS - If you can't find the answers there, find the works of Jacobsen, Molander, Danheiser, Nikolau, et. al....