Development of an enantioselective, kilogram-scale, rhodium-catalysed 1,4-addition

Organic Process Research and Development

Volumn 12, Issue 3, 2008, Pages 496-502

  Brock, Sally ^a   Hose, David R J ^a   Moseley, Jonathan D ^a   Parker, Alexandra J ^a   Patel, Ian ^a   Williams, Andrew J ^a  

^a ASTRAZENECA   (United Kingdom)

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EID: 58149154348     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op700246g     Document Type: Article

References (17)

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3. Williams, A. J.; Parker, A. J. Manuscript in preparation.
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6. (a) See for example: Amengual, R.; Michelet, V.; Genet, J.-P. Synlett 2002, 1791-1794.
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14. 19F NMR]) was prepared in a 100 mL volumetric flask and made up to the mark with DMSO (nondeutrated). This stock solution was used to dilute the reaction samples (see below). The reaction was heated to 60 °C and maintained at that temperature throughout the course of the reaction. At set intervals, samples were removed (20 μL) and diluted with the DMSO stock solution (980 μL). The sampling times were 0, 15, 30. 60, 120, 180, 240, 300, 360, 420, 480, 600, 720, 840, 960, 1200, and 1440 min.
15. Williams, A. J.; Patel, I.; Oldfield, J. Int. Pat. Appl. WO2007/057643, 2007.
16. Smopex-234 is commercially available for GMP manufacture from Johnson-Matthey (http://www.smopex.com) who can also arrange for metal recovery from reaction residues.
17. Bunten, K. A.; Farrar, D. H.; Poë, A. J.; Lough, A. Organometallics 2002, 21, 3344-3350.