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• W2040541715 abstract "A set of small organic molecules catalyse reactions of unsaturated organoboron reagents with imines and carbonyls to produce amines and alcohols in high enantiomeric purity efficiently, speedily and at low cost through sustainable protocols. A team from the chemistry department of Boston College in Chestnut Hill, Massachusetts, has designed and synthesized a series of related small organic molecules capable of catalysing enantioselective transformations. Specifically, the molecules — derived from the abundant amino acid valine in a simple four-step process that uses inexpensive reagents — catalyse reactions of unsaturated organoboron reagents with imines and carbonyls. The products of the reactions are enantiomerically pure amines and alcohols that can be used to synthesize more complex, biologically active molecules for applications in chemistry, biology and medicine. The discovery of catalysts that can be used to synthesize complex organic compounds by enantioselective transformations is central to advances in the life sciences1; for this reason, many chemists aim to discover catalysts that allow for preparation of chiral molecules as predominantly one mirror-image isomer2. The ideal catalyst should not contain precious elements3 and should bring reactions to completion in a few hours through operationally simple procedures. Here we introduce a set of small organic molecules that can catalyse reactions of unsaturated organoboron reagents with imines and carbonyls; the products of the reactions are enantiomerically pure amines and alcohols, which might serve as intermediates in the preparation of biologically active molecules. A distinguishing feature of this catalyst class is the presence of a ‘key’ proton embedded within their structure. Catalysts are derived from the abundant amino acid valine and are prepared in large quantities in four steps with inexpensive reagents. Reactions are scalable, do not demand stringent conditions, and can be performed with as little as 0.25 mole per cent catalyst in less than six hours at room temperature to generate products in more than 85 per cent yield and ≥97:3 enantiomeric ratio. The efficiency, selectivity and operational simplicity of the transformations and the range of boron-based reagents are expected to render this advance important for future progress in syntheses of amines and alcohols, which are useful in chemistry, biology and medicine." @default.
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• W2040541715 date "2013-02-01" @default.
• W2040541715 modified "2023-10-12" @default.
• W2040541715 title "Simple organic molecules as catalysts for enantioselective synthesis of amines and alcohols" @default.
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• W2040541715 doi "https://doi.org/10.1038/nature11844" @default.
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