ChemInform Abstract: Preparation and Use of Aziridino Alcohols as Promoters for the Enantioselective Addition of Dialkylzinc Reagents to N-(Diphenylphosphinoyl) Imines.

✍ Scribed by P. G. ANDERSSON; D. GUIJARRO; D. TANNER

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 36 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199810037

✦ Synopsis

Preparation and Use of Aziridino Alcohols as Promoters for the Enantioselective Addition of Dialkylzinc Reagents to N-(Diphenylphosphinoyl) Imines.

-A number of new aziridino alcohols are prepared via Sharpless asymmetric aminohydroxylation and dihydroxylation or starting from readily available amino acids. The aziridino alcohol shown in condition A) is found to be the best promotor for the title reaction. The enantioselectivity is influenced by steric bulk of the side chain bearing the hydroxyl group and the stereochemistry at C-3 as well as the size of nitrogen substituent. Acidic deprotection to the corresponding free amines proceeds without racemization. Although a stoichiometric amount is essential for high enantioselectivity, about 90% of the aziridine can be recovered during work-up and reused without significant loss of chiral induction. -(ANDERSSON, P.