Chiral recyclable dimeric and polymeric Cr(III) salen complexes catalyzed aminolytic kinetic resolution of trans-aromatic epoxides under microwave irradiation

• Published in: Chirality (New York, N.Y.) N.Y.), 2007-11, Vol.19 (10), p.809-815
• Main Authors: Kureshy, Rukhsana I., Prathap, K. Jeya, Singh, Surendra, Agrawal, Santosh, Khan, Noor-Ul H., Abdi, Sayed H.R., Jasra, Raksh V.
• Format: Article
• Language: English
• Subjects: aminolytic kinetic resolution; chiral; Chromium - chemistry; Chromium - radiation effects; Cr(III) dimeric and polymeric salen; Dimerization; Epoxy Compounds - chemistry; Ethylenediamines - chemistry; Ethylenediamines - radiation effects; Microwaves; Molecular Structure; Organometallic Compounds - chemistry; Organometallic Compounds - radiation effects; Polymers - chemistry; Polymers - radiation effects; recyclable; Stereoisomerism; trans epoxides
• ISSN: 0899-0042; 1520-636X
• DOI: 10.1002/chir.20472

Aminolytic kinetic resolution (AKR) of trans‐stilbene oxide and trans‐β‐methyl styrene oxide proceeded smoothly under microwave irradiation using chiral dimeric and polymeric Cr(III) salen complexes as efficient catalysts, giving regio‐, diastereo‐, and enantioselective anti‐β‐amino alcohols in high yields (49%) and chiral purity (ee up to 94%) in case of 4‐methylaniline within 2 min. The kinetic resolution system is approximately five times faster than traditional oil bath heating at 70°C and 420 times faster than the reaction conducted at room temperature with concomitant recovery of respective chirally enriched epoxides (ee, 92%) in excellent yields (up to 48%). The catalyst 1 worked well in terms of enantioselectivity than the catalyst 2, but both the catalysts were easily recovered and reused five times with the retention of its efficiency. Chirality, 2007. © 2007 Wiley‐Liss, Inc.