38610-98-9Relevant academic research and scientific papers
Synthesis and applications of chiral organoboranes generated from sulfonium ylides
Aggarwal, Varinder K.,Guang, Yu Fang,Schmidt, Andreas T.
, p. 1642 - 1643 (2005)
The reactions of aryl-stabilized sulfonium ylides with trialkyl/triarylboranes have been investigated. Clean monohomologation of the boranes with only a small amount of the higher homologation products (2O2/NaOH) and amines (treatment with NH2OSO3H). Although the reactions were conveniently conducted at 5 °C, the ylide reaction with tributylborane was very fast even at -78 °C (complete after 15 min). Use of chiral sulfides rendered the reactions asymmetric, and high enantioselectivity (>95% ee) was observed in all cases. The ylide-borane reaction was applied to short syntheses of the anti-inflammatory agents neobenodine and cetirizine, both of which contain a chiral diarylmethylalkoxy and diarylmethylamino moiety, respectively. Copyright
