Luoting Yu

Bio: Luoting Yu is an academic researcher from Sichuan University. The author has contributed to research in topics: Michael reaction & Enantioselective synthesis. The author has an hindex of 3, co-authored 4 publications receiving 399 citations. Previous affiliations of Luoting Yu include Chinese Academy of Sciences.

Novel Small Organic Molecules for a Highly Enantioselective Direct Aldol Reaction

Abstract: Novel organic molecules containing an l-proline amide moiety and a terminal hydroxyl for catalyzing direct asymmetric aldol reactions of aldehydes in neat acetone are designed and prepared. Catalyst 3d, prepared from l-proline and (1S,2S)-diphenyl-2-aminoethanol, exhibits high enantioselectivities of up to 93% ee for aromatic aldehydes and up to >99% ee for aliphatic aldehydes. A theoretical study of transition structures demonstrates the important role of the terminal hydroxyl group in the catalyst in the stereodiscrimination. Our results suggest a new strategy in the design of new organic catalysts for direct asymmetric aldol reactions and related transformations because plentiful chiral resources containing multi-hydrogen bond donors, for example, peptides, might be adopted in the design.

Organocatalytic asymmetric Michael reaction with acylsilane donors

Abstract: We have developed an organocatalytic asymmetric Michael reaction of acylsilane through the selection of acylsilane substrates and organocatalysts, thus creating a rare example of acylsilane α-alkylation with a chiral guanidine catalyst, which afforded products in good yields and high stereoselectivity. The corresponding adducts described here have also been demonstrated to be useful in the synthesis of unnatural amino acids and biologically active compounds.

Novel Small Organic Molecules for a Highly Enantioselective Direct Aldol Reaction.

Abstract: Novel organic molecules containing an l-proline amide moiety and a terminal hydroxyl for catalyzing direct asymmetric aldol reactions of aldehydes in neat acetone are designed and prepared. Catalyst 3d, prepared from l-proline and (1S,2S)-diphenyl-2-aminoethanol, exhibits high enantioselectivities of up to 93% ee for aromatic aldehydes and up to >99% ee for aliphatic aldehydes. A theoretical study of transition structures demonstrates the important role of the terminal hydroxyl group in the catalyst in the stereodiscrimination. Our results suggest a new strategy in the design of new organic catalysts for direct asymmetric aldol reactions and related transformations because plentiful chiral resources containing multi-hydrogen bond donors, for example, peptides, might be adopted in the design.

Organocatalytic Asymmetric Michael Reaction with Acylsilane Donors.

Abstract: We have developed an organocatalytic asymmetric Michael reaction of acylsilane through the selection of acylsilane substrates and organocatalysts, thus creating a rare example of acylsilane α-alkylation with a chiral guanidine catalyst, which afforded products in good yields and high stereoselectivity. The corresponding adducts described here have also been demonstrated to be useful in the synthesis of unnatural amino acids and biologically active compounds.

Asymmetric catalysis by chiral hydrogen-bond donors.

Abstract: Hydrogen bonding is responsible for the structure of much of the world around us. The unusual and complex properties of bulk water, the ability of proteins to fold into stable three-dimensional structures, the fidelity of DNA base pairing, and the binding of ligands to receptors are among the manifestations of this ubiquitous noncovalent interaction. In addition to its primacy as a structural determinant, hydrogen bonding plays a crucial functional role in catalysis. Hydrogen bonding to an electrophile serves to decrease the electron density of this species, activating it toward nucleophilic attack. This principle is employed frequently by Nature's catalysts, enzymes, for the acceleration of a wide range of chemical processes. Recently, organic chemists have begun to appreciate the tremendous potential offered by hydrogen bonding as a mechanism for electrophile activation in small-molecule, synthetic catalyst systems. In particular, chiral hydrogen-bond donors have emerged as a broadly applicable class of catalysts for enantioselective synthesis. This review documents these advances, emphasizing the structural and mechanistic features that contribute to high enantioselectivity in hydrogen-bond-mediated catalytic processes.

Asymmetric aminocatalysis--gold rush in organic chemistry.

Abstract: Catalysis with chiral secondary amines (asymmetric aminocatalysis) has become a well-established and powerful synthetic tool for the chemo- and enantioselective functionalization of carbonyl compounds. In the last eight years alone, this field has grown at such an extraordinary pace that it is now recognized as an independent area of synthetic chemistry, where the goal is the preparation of any chiral molecule in an efficient, rapid, and stereoselective manner. This has been made possible by the impressive level of scientific competition and high quality research generated in this area. This Review describes this "Asymmetric Aminocatalysis Gold Rush" and charts the milestones in its development. As in all areas of science, progress depends on human effort.

The Direct Catalytic Asymmetric Aldol Reaction

Abstract: Asymmetric aldol reactions are a powerful method for the construction of carbon–carbon bonds in an enantioselective fashion. Historically this reaction has been performed in a stoichiometric fashion to control the various aspects of chemo-, diastereo-, regio- and enantioselectivity, however, a more atom economical approach would unite high selectivity with the use of only a catalytic amount of a chiral promoter. This critical review documents the development of direct catalytic asymmetric aldol methodologies, including organocatalytic and metal-based strategies. New methods have improved the reactivity, selectivity and substrate scope of the direct aldol reaction and enabled the synthesis of complex molecular targets (357 references).