Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2018, Issue 29, Pages 3992-3996Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201800459
Keywords
Asymmetric catalysis; Organocatalysis; Dual-reagent catalysis; Chirality; Cyanosilylation
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Funding
- Science and Technology Commission of Shanghai Municipality [15ZR1409200]
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The first highly enantioselective cyanosilylation of ,-dialkoxy ketones enabled by a dual-reagent catalysis has been developed. With the combination of a chiral bifunctional phosphine-thiourea and methyl acrylate, the key organophosphorus zwitterion intermediate was generated in situ as a novel Lewis base, which catalyzed the enantioselective cyanosilylation reaction in excellent yields (up to 99%) with good-to-excellent enantioselectivities (up to 94% ee).
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