Indium-Bipyridine Catalyzed, Enantioselective Aminolysis of meso-Epoxides

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.

amine - asymmetric catalysis - bipyridine - epoxides - ­indium

References and Notes

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<A NAME="RG09707ST-13">13</A>

We have made the same observation in the related indium(III)-bipyridine 2a catalyzed thiolysis of meso-epoxides (ref. 9).

<A NAME="RG09707ST-14">14</A>

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.

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