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DOI: 10.1055/s-2007-984902
Indium-Bipyridine Catalyzed, Enantioselective Aminolysis of meso-Epoxides
Publication History
Publication Date:
17 July 2007 (online)
Abstract
The enantioselective aminolysis of meso-epoxides is efficiently catalyzed by an indium(III)-bipyridine catalyst to furnish highly enantiomerically enriched 1,2-amino alcohols in good yields and up to 98% ee.
Key words
amine - asymmetric catalysis - bipyridine - epoxides - indium
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References and Notes
We have made the same observation in the related indium(III)-bipyridine 2a catalyzed thiolysis of meso-epoxides (ref. 9).
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Typical Experimental Procedure
In an oven-dried flask and under inert atmosphere In(OTf)3 (28 mg, 0.05 mmol) and bipyridine 2a (20 mg, 0.05 mmol) were dissolved in CH2Cl2 (1 mL) and treated with epoxide (0.50 mmol) and amine (1.00 mmol) at r.t. The reaction mixture was stirred for 48 h at r.t. whereupon it was concentrated in vacuo and purified by silica gel chromatography. For analytical and spectroscopic details of the products, see ref. 8b.