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Chiral recyclable dimeric and polymeric Cr(III) salen complexes catalyzed aminolytic kinetic resolution of trans ‐aromatic epoxides under microwave irradiation
Author(s) -
Kureshy Rukhsana I.,
Prathap K. Jeya,
Singh Surendra,
Agrawal Santosh,
Khan NoorUl H.,
Abdi Sayed H.R.,
Jasra Raksh V.
Publication year - 2007
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20472
Subject(s) - chemistry , kinetic resolution , microwave irradiation , catalysis , metal salen complexes , polymer chemistry , kinetic energy , irradiation , resolution (logic) , photochemistry , organic chemistry , combinatorial chemistry , enantioselective synthesis , physics , artificial intelligence , computer science , nuclear physics , quantum mechanics
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.