title: Simple organic molecules as catalysts for enantioselective synthesis of amines and alcohols.
abstract: The discovery of catalysts that can be used to synthesize complex organic compounds by enantioselective transformations is central to advances in the life sciences; for this reason, many chemists aim to discover catalysts that allow for preparation of chiral molecules as predominantly one mirror-image isomer. The ideal catalyst should not contain precious elements 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.
authors: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
authors: Daniel L
authors: DL
authors: Silverio
authors: Sebastian
authors: S
authors: Torker
authors: Tatiana
authors: T
authors: Pilyugina
authors: Erika M
authors: EM
authors: Vieira
authors: Marc L
authors: ML
authors: Snapper
authors: Fredrik
authors: F
authors: Haeffner
authors: Amir H
authors: AH
authors: Hoveyda
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D001895:Boron / Q000737:chemistry; D002384:Catalysis; D007097:Imines / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D011522:Protons; D013237:Stereoisomerism; D013696:Temperature; D013997:Time Factors; D014633:Valine / Q000031:analogs & derivatives* / Q000737:chemistry*
chemical_list: D000438:Alcohols; D000588:Amines; D007097:Imines; D007202:Indicators and Reagents; D011522:Protons; D014633:Valine; D001895:Boron