[kriggy]

Hey there, my department is doing some  "renovation" of our masters level classes next year and Im somehow little bit involved in this. Lets say today at a meeting I mentioned that I think our curriculum at masters level doesnt really improve our knowledge of organic chemistry and we could do better. In a sense, our undergrad ochem class is not going into deep details because its mandatory for biochemists and other fields that doesnt need that deep detail and we dont have enough manpower to have separate class for our undergrads. (think they learn aldol reaction but not how to control stereochemistry, they learn wittig reaction but dont how to controll E/Z selectivity, they learn diels-alder but not going into detail what happens if you change the configuration of double bonds in starting material etc...).

Anyway, I dont want be criticizing only but I would like to suggest some improvement, which might end up being a new class for our master level studens. In my mind, it should describe those more advanced topics to students that are focusing on organic chemistry. Obviously, Im just a grad student so I dont have much experience  so here I am asking for your help. Think 12 weeks of classes with 90-135 minute classes per week, which topic should be covered in your opinion?

1) aldol reactions - stereochemistry control,
2) enolate chemistry - asymmetric alkylation, enamine chemistry,
3) cycloadditions - Huisgen cycloaddition, diels alder reaction - stereochemistry control, hetero-DA reations
4) olefin chemistry - olefination reactions (witting and variants, Julia, Julia-kochensky), methathesis reactions
5) addition to carbonyl compounds - asymmetric reductions, 1,2 vs 1.4 addition etc..
6) oxidation and reductions - reduction of double bonds
7) arylation reactions - chan-lam, buchwald-hartwing
8 ) coupling reactions - suzuki, stille etc.. 7 and 8 should cover general aspects such as "is boronic acid in chan-lam/suzuki with EDG more or less reactive?" in a sense that the students should recognize if the given reaction is going to be somehow "tricky" or not
9) ? Peptide chemistry + acylation reactions?
10) ? Protecting groups?
11) ?
12) ?

My idea is that each class will focus on one of the topics because then multiple people can teach. Might not be the best idea but I feel if we have someone experienced in for example, peptide chemistry why he/she shouldnt have one lecture focusing on that topic. Of course, it brings different problems as we learned from another class which was taught by multiple people but if done right and coordinated it should work.

What do you think?

[Babcock_Hall]

Speaking as a biochemist who uses organic chemistry, I think that including protecting groups is helpful.  I have had syntheses go wrong at the stage of removing the protecting group.  I also have seen instances where the wrong choice of a protecting group wasted time.

[hypervalent_iodine]

Your list looks to more or less cover what I did in my honours year class plus third year O chem, the former of which is equivalent to masters in some places. This was what we did in honours (or what I remember of it; it was 9 years ago):

Module 1
Organometallics - Suzuki, Heck, Negishi, Grubbs (inc. catalytic cycles, catalyst design, etc)

Module 2
Chiral auxiliaries - Evan's auxiliary (esp. their use in asymmetric DA reactions and Diekmann cyclisation), sulfoxides,
Methods for determining configuration / kinetic resolution - Horeau's method, Moshers ester, XRD
Chirality in compounds without stereogenic centres - Allenes, biphenyls, spiranes, etc.
Stereoelectronic effects governing configuration of esters and amides
Baldwin's rules
Stereoselectivity/specificity of aldol reactions
Anomeric effect
Enzymatic reactions

Module 3
Complex NMR assignments
HSQC
NOESY / ROSEY
HMBC
COSY

Module 4
Total synthesis (students were assigned a molecule from Nicolaou's book and had to present a lecture on it, with time for questions).


For background, in third year advanced organic we cover pericyclic chemistry (including constructing HOMO/LUMO diagrams, predicting stereochemistry, Woodward Hoffman rules, etc.), asymmetric synthesis (including Sharpless, proline catalysis, chiral pool, kinetic resolution, probably something else), retrosynthesis, and another module best described as miscellaneous (I recall we did a bit of radical chemistry, tin reactions, AIBN, etc). In another subject we cover sugar chemistry and protecting groups.