Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 349, Issue 3, Pages 343-349Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200600336
Keywords
aldehyde; asymmetric catalysis; C-C bond formation; cyanoethoxycarbonylation; cyanohydrins; ethyl carbonates
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Highly efficient catalytic asymmetric cyanoethoxycarbonylation of aldehydes was achieved by 10 mol% cinchonine with 10 mol% heterometallic (S)-aluminum lithium bis(binaphthoxide), which gave the cyanohydrins ethyl carbonates in excellent isolated yields (up to 99%) with moderate to high enantioselectivities (up to 95 % ee) under mild conditions (at -20 degrees C). Especially, the solid aluminum lithium bis(binaphthoxide) free of tetrahydrofuran was obtained by a new procedure using (S)-bi(2-naphthol), aluminum isopropoxide and n-butyllithium in dichloromethane, which was insensitive to air and moisture and was very convenient to store and use. A catalytic cycle based on experimental phenomena was proposed to explain the nature of the asymmetric induction.
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