Catalytic Asymmetric Activation of a C sp 3[BOND]H Bond Adjacent to a Nitrogen Atom: A Versatile Approach to Optically Active α-Alkyl α-Amino Acids and C1-Alkylated Tetrahydroisoquinoline Derivatives - Zhang - 2011 - Angewandte Chemie International Edition - Wiley Online Library - http://onlinelibrary.wiley.com/doi...
"10.1002/anie.201105123" Combination of Cu and DDQ, but not surprising given Li's example of a similar reaction with alkynes.
- Matthew Todd
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Thank you to everyone here for your help, support, encouragement on this project, which has made an enormous difference. The project is still going, but this paper represents a milestone in what we set out to do. We have a commentary coming out on Friday about open science more generally which I hope people will find interesting.
- Matthew Todd
Did you ask to post the spectra as .jdx too - only pdf available - are the jdx versions available on your open notebook?
- Andrew Lang
...but I think we're going to start an experiment with posting the raw NMR data rather than .dx and see how that goes.
- Matthew Todd
We should look at pulling that raw data down and converting to JCAMP/AniML for you in automated fashion. Having just this discussion around some other data at a meeting with JGF and co at the moment.
- Cameron Neylon
Would be v nice. We can post raw data on a sample post as a sandbox if you like - just say the word.
- Matthew Todd
I will see whether sufficient of the pieces are in place but does the following appeal in principle? Directory exists on some computer. When new raw NMR file is dropped in that directory a local GUI pops up to ask some q about metadata. When questions answered raw data gets pushed to LabTrove instance. Service monitors a specific feed for new raw data. When it sees some it processes to...
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- Cameron Neylon
Congratulations! And that commentary has one of the coolest titles ever.
- Daniel Mietchen
I am in for playing a bit with the MR spectra, though I am more of an imaging guy.
- Daniel Mietchen
Is it your group who are going to run the assays or someone in India?
- Andrew Lang
Well, assays can of course we run by anyone. We have a couple of excellent labs lined up for this - one is Eskitis in Queensland, and the other is the Ralph lab at Uni Melbourne. The main bottleneck is at this point synthetic medicinal chemistry.
- Matthew Todd
Transition metal-catalyzed cross coupling with N-acyliminium ions derived from quinolines and isoquinolines - Chemical Science (RSC Publishing) - http://pubs.rsc.org/en...
Cyclization via Pictet-Spengler reaction gave diastereo-enriched dihydroisoquinolines which can be separated and converted to the enantiopure product
- Michael Wolfle
Dehydrogenative Functionalization of C(sp3)–H Bonds Adjacent to a Heteroatom Mediated by Oxoammonium Salts - Richter - 2010 - European Journal of Organic Chemistry - Wiley Online Library - http://onlinelibrary.wiley.com...
Efficient and chemoselective alkylation of amines/amino acids using alcohols as alkylating reagents under mild conditions - Chemical Communications (RSC Publishing) - http://pubs.rsc.org/en...
10.1039/C0CC01487G. Pretty. Very selective N-methylation, presumably discovered as a byproduct from a debenzylation reaction. This must be known, but the selectivity is still very nice.
- Matthew Todd
from Bookmarklet
This is a typical de-benzylation condition and i used many a times, never observed any alkylation. Table-2 entry-9. Proline to N-ethylproline in 85% yield? using 10%Pd/C in EtOH. Not done a reaction with a MeOD. Im not impressed.
- Ahamed
secondary alcohols oxidized to the corresponding ketone without oxidants under the hydrogenation conditions, see this paper. http://pubs.acs.org/doi...
- Ahamed
So MeOH ------> HCHO which then forms imine and this imine gets reduced under Pd/C, H2 conditions. The first part is strange.
- Ahamed
"The Commonwealth gave Sydney University $750 million in grants in 2009 – before you get to HECS payments and student fees. About $200 million a year goes to the faculty of medicine for research. Those funds employ a small army of very clever men and women in trying to solve human health-related problems. Sydnovate's sole purpose is to commercialise the good ideas that this army of researchers (and their colleagues in the faculties of engineering, chemistry, etc) create. So what is the royalty return that we taxpayers get for $750 million a year? It's $2.5 million in 2009 out of total university revenue of $1.4 billion – or one-third of 1 per cent. After 160 years of operation, Sydney University makes more money selling beer and hamburgers to students than it does licensing intellectual property."
- Matthew Todd
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Zinc-prolinamide complex catalyzed direct asymmetric aldol reactions in the presence of water, SpringerLink - SCIENCE CHINA Chemistry, Volume 53, Number 11 - http://www.springerlink.com/content...
10.1007/s11426-010-4069-x, Ahamed - zinc plus organocatalyst for aldol
- Matthew Todd
from Bookmarklet
thanks, there is a good increase in ee when Zn(OTf)2 was used in combination with chiral catalyst, however the yields havent changed which is strange.
- Ahamed
"10.1021/ol101576q" Althea - use of dimethylaniline substrates, here in an Ugi-like process, but the principle remains the same. Cu plus a ligand plus peroxide.
- Matthew Todd
from Bookmarklet
A nice reaction to explore its asymmetric version. Chiral Py-BOX??
- Ahamed
"The Nobel laureate John Cornforth said it well: he defined the perfect synthesis as one which could be done by a one-armed operator by pouring down a mixture of chemicals down a drain and collecting the product in one hundred percent yield and stereoselectivity at the other end." - this is what we are doing with most of our projects with PZQ. I love this definition.
- Ahamed
Subtilisin as a useful peptide cleaver that accepts unnatural things nearby its cleavage site - Mingfeng look what the enzyme's doing here: 10.1039/B914358K. Also a simple peptide. And short.
Drug Praziquantel Fights Schistosomiasis, But Too Expensive for Africa | Smart Journalism. Real Solutions. Miller-McCune. - http://www.miller-mccune.com/health...
"“Schistosomiasis is a far more important disease than we ever realized,” said Peter Hotez, one author of the commentary and the chairman of the department of microbiology, immunology, and tropical medicine at The George Washington University. “The failure of the global community to provide access to this essential medicine is impeding sustainable development in Africa.”"
- Matthew Todd
from Bookmarklet
Efficient Multicomponent Reaction Synthesis of the Schistosomiasis Drug Praziquantel - Cao - 2010 - Chemistry – A European Journal - http://onlinelibrary.wiley.com/doi...
The long awaited Domling paper on the Ugi synthesis approach to praziqantel. The yield is reported as 100% in a scheme, it is 98% in the experimental section. I would like to see the NMR of that product but it isn't in the supplementary materials. We've never seen any Ugi reaction that close to quantitative. Also no mention of whether a precipitate forms.
- Jean-Claude Bradley
Well look at that - another anthelmintic where one enantiomer is active and where the structure is based on a chiral vicinal diamine!
- Matthew Todd
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