β-Siloxy-α-haloketones through Highly Diastereoselective Single and Double Mukaiyama Aldol Reactions
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چکیده
منابع مشابه
Highly Diastereoselective Aldol Reactions of Chiral Methyl Ketones
Diastereoselective aldol additions have emerged as one of the most efficient and versatile methods available for preparing a wide range of optically active compounds.l Very high diastereoselectivities have been reported for aldol reactiona involving chiral enolates derived from a-ethylor higher alkyl-substituted ketone derivatives. By contrast, relatively few examples of highly diastereoselecti...
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A highly diastereoselective approach for the synthesis of protected a,b-dioxyaldehydes derived from (Z)tris(trimethylsilyl)silyl “super silyl” enol ethers is described. A general and highly syn-stereoselective aldol reaction directed by the “super silyl” group catalyzed by triflimide (HNTf2) is developed providing a,bdioxyaldehydes and 1,2,3-triol fragments which can be a useful platform for th...
متن کاملHighly diastereoselective vinylogous Mukaiyama aldol reaction of α-keto phosphonates with 2-(trimethylsilyloxy)furan catalyzed by Cu(OTf)2.
The diastereospecific formation of δ-hydroxyalkylbutenolide phosphonate has been achieved via a vinylogous Mukaiyama aldol reaction. The reaction was performed using α-ketophosphonate 1 and 2-(trimethylsilyloxy)furan 2 mediated by Cu(OTf)(2) and 2,2,2-trifluoroethanol as additive in CH(2)Cl(2). The reaction proceeds rapidly and affords the corresponding 5-(hydroxy(aryl)methyl) furan-2(5H)-one p...
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 کاملDisulfonimide-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...
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ژورنال
عنوان ژورنال: Chemistry - A European Journal
سال: 2013
ISSN: 0947-6539
DOI: 10.1002/chem.201204493