Rhodium-Catalysed Asymmetric Hydroformylation of Unsaturated Nitriles

✍ Scribed by Mariëlle M. H. Lambers-Verstappen; Johannes G. de Vries

• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: English
• Weight: 79 KB
• Volume: 345
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/adsc.200390053

✦ Synopsis

Abstract

Asymmetric hydroformylation of crotononitrile (1) and ally cyanide (2) was probed with the view to develop a synthesis for (R)‐4‐amino‐2‐methyl‐butan‐1‐ol. Hydroformylation of 1 under a variety of conditions mainly led to hydrogenated product. Hydroformylation of 2 with Rh/tris(2,4‐di‐tert‐butylphenyl) phosphite gave good selectivity to the formylated nitrile with an n/iso of 77:23. Asymmetric hydroformylation of 2 could be accomplished in 66% ee using Rh/(R,S)‐BINAPHOS.