Chiral Hypervalent Organo-Iodine(III) Compounds

✍ Scribed by Urs H. Hirt; Martin F. H. Schuster; Andrew N. French; Olaf G. Wiest; Thomas Wirth

• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 431 KB
• Volume: 2001
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/1099-0690(200104)2001:8<1569::aid-ejoc1569>3.0.co;2-t

✦ Synopsis

A series of ortho-substituted chiral hypervalent iodine reagents has been synthesized utilizing a zirconium-mediated iodoacylation reaction, which was followed by a stereoselective reduction, methylation, and an oxidation/ligand-exchange sequence. The evaluation of these new compounds as stereoselective electrophilic reagents towards alkenes and ketones is reported. Enantioselectivities as high as 65% have been achieved in the dioxytosylation of styrene and of up to 40% in the oxytosylation of propiophenone. X-ray structure [a]