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Improved catalytic activity of homochiral dimeric cobalt–salen complex in hydrolytic kinetic resolution of terminal racemic epoxides

✍ Scribed by Rukhsana I. Kureshy; Surendra Singh; Noor-Ul H. Khan; Sayed H.R. Abdi; Irshad Ahmad; Achyut Bhatt; Raksh V. Jasra

Publisher: John Wiley and Sons
Year: 2005
Tongue: English
Weight: 97 KB
Volume: 17
Category: Article
ISSN: 0899-0042
DOI: 10.1002/chir.20196

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✦ Synopsis

Abstract

Enantiomerically pure epoxides (99%, ee) and diols (98%, ee) from racemic epichlorohydrin, 1,2‐epoxypropane, 1,2‐epoxyhexane, 1,2‐epoxyoctane, and 1,2‐epoxydodecane were obtained in 2–12 h by hydrolytic kinetic resolution (HKR) using the recyclable dimeric homochiral Co(III)–salen complex 1′ (0.2 mol %) derived from 5,5‐(2′,2′‐dimethylpropane)‐di‐[(R,R)‐{N‐(3‐tert‐butylsalicylidine)‐N′‐(3′,5′‐di‐tert‐butylsalicylidine)}‐1,2‐cyclohexanediamine] with cobalt(II) acetate. Unlike its monomeric version, the catalyst could be recycled several times without loss in performance. The use of BF~4~ as counter ion in HKR reactions was also investigated. © 2005 Wiley‐Liss, Inc. Chirality 17:590–594, 2005.

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