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Absolute Asymmetric Synthesis of Enantiopure Organozinc Reagents, Followed by Highly Enantioselective Chlorination

Journal article
Authors Susanne Olsson
Anders Lennartson
Mikael Håkansson
Published in Chemistry - A European Journal
Volume 19
Issue 37
Pages 12415-12423
ISSN 0947-6539
Publication year 2013
Published at Department of Chemistry and Molecular Biology
Pages 12415-12423
Language en
Links dx.doi.org/10.1002/chem.201301465
Keywords asymmetric synthesis, chirality, crystal growth, enantioselectivity, total spontaneous resolution, zinc
Subject categories Polymer Chemistry

Abstract

We report the absolute asymmetric synthesis (AAS) of indenylzinc reagents by using total spontaneous resolution followed by enantiospecific conversion into 1-chloroindene. The chiral complex [Zn(dcp)(ind)(tmeda)] (dcp=2,6-dichlorophenoxy and tmeda=N,N,N,N-tetramethylethylenediamine) (3) was prepared from the achiral starting materials indene, potassium, zinc chloride, TMEDA, and 2,6-dichlorophenol. The reagent resolved spontaneously on crystallization, and single crystals of 3 react with N-chlorosuccinimide in the presence of benzoquinone in 2-propanol to give 1-chloroindene in >98% enantiomeric excess. It was found that (R)-3 gave (R)-1-chloroindene upon reaction, indicating an S(E)2-mechanism. Since bulk samples of 3 gave optically active product upon chlorination, total spontaneous resolution must have occurred. This demonstrates that enantiopure products can be obtained through the absolute asymmetric synthesis of organometallic reagents starting from achiral materials. The general absolute asymmetric synthesis (AAS) method offers easy access to both enantiomers and an almost limitless variation in the design of the product.

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