Issue 39 August/September 2011

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What's New in Process Chemistry?
Newsletter Issue 39 August/September 2011.
Scientific Updates' What's New in Process ChemistryScientific Update
What's New in Process Chemistry.
Dihydropyridones from Formamides

Dr John Knight
T Hiyama et al (JACS, 2011, 133, (10), 3264) describe a dehydrogenative nickel catalysed reaction which results in the formation of dihydropyridones from a formamide and an acetylene. The paper contains 13 examples with isolated yields ranging from just 23% up to an impressive >95%.

Organocatalysed Asymmetric C-H Activation

Dr John Knight
T Akiyama et al (JACS, 2011, 133, (16), 6166) report an interesting reaction where organocatalysis has been used to achieve activation of a C-H bond via what is described as an overall internal redox process to generate tetrahydroquinolines in 9 of the 11 examples shown, with >90%ee from achiral starting material.

Asymmetric Aldol Reaction in Brine 1

Dr John Knight
T Miura et al (SYNLETT, 2011, (3), 410) describe an organocatalysed asymmetric aldol reaction which is carried out in brine solution.  The typical procedure describes mixing the aldehyde with the ketone in brine in the presence of catalytic quantities of TFA and the organocatalyst and stirring the mixture at room temperature for 36h.

Asymmetric Aldol Reaction in Brine 2

Dr John Knight
W R Jackson et al (SYNLETT, 2011, (6), 831) describe an unexpected reaction of DMF to form tetramethylguanidines. The intended chemistry was the base-mediated removal of an fmoc protecting group in DMF as solvent, but the group found considerable extent of the by-product ...

Odourless Thio-Beckmann Rearrangement

Dr Will Watson
This paper describes an odourless one-pot process for conversion of oximes to thioamides.  The oxime is initially reacted with tosyl chloride and triethylamine at 0ºC in acetonitrile. 

New Amine Protecting Group

Dr Will Watson
Scientists at Pfizer have recently published a new protecting group for amines – the Mpoc group.  This is essentially the Boc group where two methyl groups have been joined together to form a cyclopropane ring, but this minor change in structure results in a large change in stability / reactivity. 

A New Twist on the Fischer Indole Synthesis

Dr Will Watson
In the traditional Fischer Indole Synthesis an aromatic hydrazine is reacted with a ketone and then cyclized to produce the indole.  This new twist from Paul Knochel’s group is to react organozinc reagents with aromatic diazonium salts at -60ºC in THF. 

New Books
Silver in Organic Chemistry (ed Michael Harmata)
Wiley 2010 - £73.50
Solvent and Solvent Effects in Organic Chemistry (4th Updated and Enlarged Edition) by C Reichardt and T Welton
Wiley-VCH, 2011 - £130
Practical Synthetic Organic Chemistry: Reactions, Principles and Techniques (ed S Caron)
Wiley 2011, 872 pages - £60.50
Why Not Exhibit at one of our Events?

View our recent Conference Scale-Up of Chemical Processes in July at the Colonnade Hotel in Boston, MA, USA and see comments from Kathleen Battista of HEL, Alan Cramey of Ace Glass, Yuhshuh Kao of Johnson Matthey, Dr Zsolt Bencze of Ubichem, Albert Pacella of Albermarle and Dr Gilda Gasparini of AM Technology - all of whom were Exhibitors/Attendees at this event.

... and finally - you might be an engineer if......

... ... you spent more on your calculator than you did on your wedding ring.

Dates for your diary...
Click to view our 2011 Conference and Course Dates

CONFERENCES
Organic Process Research & Development
19 - 21 September 2011
Budapest, Hungary
Developing Chemical Processes for Active Pharmaceutical Ingredients (APIs)
6 & 7 February 2012
Mumbai, India
Organic Process Research & Development
19 - 21 March 2012
San Francisco, CA, USA
Modern Synthetic Methods and Chiral Europe
14 - 16 May 2012
Prague, Czech Republic
The Scale-Up of Chemical Processes
9 - 11 July 2012
Milan, Italy

COURSES
Secrets of Batch Process Scale-Up
14 - 16 September 2011
Edinburgh, Scotland
Advanced Aromatic Heterocyclic Chemistry
27 - 29 September 2011
Basel, Switzerland
The Design, Development and Scale-Up of Safe Chemical Processes and Operations
28 - 30 September 2011
Princeton, USA
Chemical Development & Scale-Up in the Fine Chemical & Pharmaceutical Industries
3 - 5 October 2011
Memphis, TN, USA
ADME and hERG in Medicinal Chemistry
4 - 5 October 2011
Edinburgh, Scotland


OTHER EVENTS
Genotoxic Impurities
20 September 2011
Budapest, Hungary
Grignards in Process R&D
20 September 2011
Budapest, Hungary


Stretch your training budget - register 2 or more delegates and SAVE up to 15%!

20 years and still as popular as ever..

Chemical Development & Scale Up in the Fine Chemical & Pharmaceutical Industries is our most popular Training Course. If you have attended this Course, we'd like to hear from you.

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Seeing is believing.
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