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Asymmetric Hydrolytic Kinetic Resolution with Recyclable Macrocyclic Co(III) -Salen Complexes: A Practical Strategy in the Preparation of (R)-Mexiletine and (S)-Propranolol.
MedLine Citation:
PMID:  22422658     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
A chiral cobalt(III) complex (1 e) was synthesized by the interaction of cobalt(II) acetate and ferrocenium hexafluorophosphate with a chiral dinuclear macrocyclic salen ligand that was derived from 1R,2R-(-)-1,2-diaminocyclohexane with trigol bis-aldehyde. A variety of epoxides and glycidyl ethers were suitable substrates for the reaction with water in the presence of chiral macrocyclic salen complex 1 e at room temperature to afford chiral epoxides and diols by hydrolytic kinetic resolution (HKR). Excellent yields (47 % with respect to the epoxides, 53 % with respect to the diols) and high enantioselectivity (ee>99 % for the epoxides, up to 96 % for the diols) were achieved in 2.5-16 h. The Co(III) macrocyclic salen complex (1 e) maintained its performance on a multigram scale and was expediently recycled a number of times. We further extended our study of chiral epoxides that were synthesized by using HKR to the synthesis of chiral drug molecules (R)-mexiletine and (S)-propranolol.
Authors:
Arghya Sadhukhan; Noor-Ul H Khan; Tamal Roy; Rukhsana I Kureshy; Sayed H R Abdi; Hari C Bajaj
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-3-15
Journal Detail:
Title:  Chemistry (Weinheim an der Bergstrasse, Germany)     Volume:  -     ISSN:  1521-3765     ISO Abbreviation:  -     Publication Date:  2012 Mar 
Date Detail:
Created Date:  2012-3-16     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9513783     Medline TA:  Chemistry     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Affiliation:
Discipline of Inorganic Materials and Catalysis, Central Salt and Marine Chemicals Research, Institute (CSMCRI), Council of Scientific & Industrial Research (CSIR), G. B. Marg, Bhavnagar- 364 021, Gujarat (India), Fax: (+91) 0278-2566970.
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