Diastereoselectivity in Lewis-Acid-Catalyzed Mukaiyama Aldol Reactions: A DFT Study
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چکیده
منابع مشابه
Disulfonimide-catalyzed asymmetric vinylogous and bisvinylogous Mukaiyama aldol reactions.
The term vinylogy, which describes a unique property of p systems where the electron density and reactivity is amplified along conjugated bonds, was proposed 75 years ago by Fuson. The principle becomes particularly relevant in the context of the aldol reaction: While metal dienolates often furnish mixtures of aand g-addition products, the corresponding dienolsilanes react with high selectivity...
متن کاملMukaiyama Aldol Reactions in Aqueous Media
Mukaiyama aldol reactions in aqueous media have been surveyed. While the original Mukaiyama aldol reactions entailed stoichiometric use of Lewis acids in organic solvents under strictly anhydrous conditions, Mukaiyama aldol reactions in aqueous media are not only suitable for green sustainable chemistry but are found to produce singular phenomena. These findings led to the discovery of a series...
متن کاملStudy of the lanthanide-catalyzed, aqueous, asymmetric Mukaiyama aldol reaction.
The development of efficient methods for the asymmetric Mukaiyama aldol reaction in aqueous solution has received great attention. We have developed a new series of chiral lanthanide-containing complexes that produce Mukaiyama aldol products with outstanding enantioselectivities. In this paper, we describe an optimized ligand synthesis, trends in stereoselectivity that result from changing lant...
متن کاملA new class of ligands for aqueous, lanthanide-catalyzed, enantioselective Mukaiyama aldol reactions.
The development of aqueous methods for generating enantiopure β-hydroxy carbonyl compounds is an important goal because these subunits compose many bioactive compounds and the ability to synthesize these groups in water has environmental and cost benefits. In this communication, we report a new class of ligands for aqueous, lanthanide-catalyzed, asymmetric Mukaiyama aldol reactions for the synt...
متن کاملAn environmentally friendly Mukaiyama aldol reaction catalyzed by a strong Brønsted acid in solvent-free conditions.
o-Benzenedisulfonimide, a new strong bench-stable Brønsted acid, has been shown to efficiently catalyze the Mukaiyama aldol reaction of aldehydes or dimethyl acetals with silyl enol ethers under mild solvent-free reaction conditions.
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ژورنال
عنوان ژورنال: Journal of the American Chemical Society
سال: 2012
ISSN: 0002-7863,1520-5126
DOI: 10.1021/ja3052975