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Today I managed to prepare 3 imines (started AND finished. Chuffed indeed) - the starting materials for the Pictet-Spengler reaction model (

Lab notes here:

For the next 8-9 weeks I'll be working on the asymmetric Lewis Acid catalysed Pictet-Spengler reaction to give substituted tetrahydroisoquinolines. I'm in the middle of preparing starting materials (most of which I completed today) and the racemic cyclised products - to use as references when developing assays for the catalytic reactions. When that's done, I'll work on screening achiral Lewis Acids, before throwing in some chiral bisoxazoline ligands (depending on how the achiral screens go, of course) and seeing what happens.

I'm also constructing a page to put a summary of the background literature research I manage to dig up - including comments/thoughts/ideas etc, as well as the progress of the project (page here: Will keep that as up to date as studently possible.

#RealTimeExperiments #openscience #chemistry
Matthew Todd's profile photo
Three imines in one day? You're on a roll. One is, as you say, a syrup. I'll be happy when the data are up and compared with lit to be sure it's meant to be a syrup. Treat the imines as air-sensitive. They're still like amines, and susceptible to oxidation. First order of business is getting the rac cyclization to work, and lit can save you a bunch of time there. Once you have product, and a nice TLC assay for conversion, you are ready to set up screens for cyclization with candidate reagents/catalysts.
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