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

被引:18
作者
Kureshy, Rukhsana I. [1 ]
Prathap, K. Jeya [1 ]
Singh, Surendra [1 ]
Agrawal, Santosh [1 ]
Khan, Noor-ul H. [1 ]
Abdi, Sayed H. R. [1 ]
Jasra, Raksh V. [1 ]
机构
[1] Cent Salt & Marine Chem Res Inst, Discipline Inorgan Mat & Catalysis, Bhavnagar 364002, Gujarat, India
关键词
aminolytic kinetic resolution; trans epoxides; chiral; Cr(III) dimeric and polymeric salen; recyclable;
D O I
10.1002/chir.20472
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Aminolytic kinetic resolution (AKR) of trans-stilbene oxide and trans-pmethyl 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-p-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 degrees 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.
引用
收藏
页码:809 / 815
页数:7
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