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Newsletter Issue 49 Sept/Oct 2013

Scientific Updates' What's New in Process ChemistryScientific Update
What's New in Process Chemistry.

Enantioselective Hydroamination


Dr John Knight

Jacobsen and colleagues (JACS, 2013, 135 (18), 6747) presented a very nice communication describing the organocatalysed generation of N-hydroxypyrrolidines with modest to high enantioselectivity.

Electrophilicities of Benzaldehyde-Derived Iminium Ions


Dr John Knight

H Mayr et al, (JACS, 2013, 135 (17), 6579) reports on the electrophilicities of benzaldehyde-derived iminium ions, producing a scale as shown below which I thought may be of use to chemists in the battle toward achieving the balance between a nucleophile and electrophile.  Good luck!

Recyclable Mitsunobu Reagents


Dr Trevor Laird

Since the Mitsunobu reaction was first introduced in 1967, it has proved an invaluable reaction in discovery chemistry yet process chemists have been reluctant to use it on large scale because of the toxicity of DEAD, thermal hazards and the difficulties with waste streams.

Atom Economical Cyclisation of Allylic Formamides to Pyrrolidones


Dr Trevor Laird

 The reaction can be extended to produce chiral pyrrolidones if chiral iridium catalysts are first used to make the allylic formamide, followed by Ru catalysed cyclisation ( J Amer Chem Soc, 2013, 135, 6814).

Asymmetric Grignard Reagent


Dr John Knight

I was intrigued to see a paper describing the formation of enantiomerically pure α-functionalised Grignard reagents (P O’Brien et al, JACS, 2013, 135 (21), 8071).  Perhaps I had missed earlier reports, but was especially interested in the generation of the configurationally stable ‘anionic’ centre.

Reductive Acetylation of Oximes...to give Substrates for Asymmetric Hydrogenation


Dr Will Watson

A few years ago chemists at Boehringer Ingelheim reported the reductive acetylation of oximes1 to produce N-acetylenamides which are good substrates for asymmetric hydrogenation.

Brain Teaser September 2013


Dr Will Watson

A few years ago chemists at Boehringer Ingelheim reported the reductive acetylation of oximes1 to produce N-acetylenamides which are good substrates for asymmetric hydrogenation.

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