Enantioselective addition of organozinc reagents to carbonyl compounds

✍ Scribed by Yus, Miguel; Ramón, Diego J.

• Book ID: 120326382
• Publisher: International Union of Pure and Applied Chemistry
• Year: 2005
• Tongue: English
• Weight: 272 KB
• Volume: 77
• Category: Article
• ISSN: 0033-4545
• DOI: 10.1351/pac200577122111

✦ Synopsis

Abstract

Different chiral camphorsulfonamide derivatives containing a hydroxy or a sulfonamido functionality, as well as chiral 1,2-hydroxysulfonamides, have been evaluated as chiral promoters in the classical enantioselective addition of dialkylzinc reagents to aldehydes in the presence of titanium tetraisopropoxide (ee up to 96 %). Surprisingly, ligands with a structure of isoborneol are able to promote the related unknown addition to ketones (ee >99 %), the best ligand being the exo-diol derived from 1,2-trans-biscamphorsulfonamidocyclohexane (HOCSAC).