Enantioselektive 1,4-Additionen von metallorganischen Verbindungen an konjugierte Systeme im chiralen Medium DDB |
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Authors: | Werner Langer Dieter Seebach |
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Abstract: | Enantioselective 1,4-additions of organometallic compounds to conjugated systems in the chiral medium DDB 1 DDB = 1,4-Dimethylamino-2,3-dimethoxybutan (= 2,3-Dimethoxy-N,N,N′,N′-tetramethyl-1,4-butandiamin). The chiral methoxyamine DDB is used as a cosolvent to add achiral Li-, Cu-, and Zn-organic compounds enantioselectively to prochiral β-carbon atoms of α, β-unsaturated aldehydes, ketones, nitro compounds and ketene-thioacetals (Tables 1 and 2). The selectivity generally ranges from 55:45 to 63:27, in one case ( 9b ) an enantiomeric excess of 43% was obtained. |
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