Hydrogen Bond Catalyzed Enantioselective Vinylogous Mukaiyama Aldol Reaction
نویسندگان
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 کاملEnantioselective synthesis of highly functionalised amides by copper-catalysed vinylogous Mukaiyama aldol reaction.
Amides with quaternary stereogenic centers have been synthesised by catalytic asymmetric vinylogous Mukaiyama aldol reactions. The chiral copper-sulfoximine catalyst gives rise to products with moderate to good yields and up to 92% ee.
متن کاملThe vinylogous Mukaiyama aldol reaction (VMAR) in natural product synthesis.
The vinylogous Mukaiyama aldol reaction (VMAR) allows efficient access to larger segments for complex natural product synthesis, primarily polyketides, through the construction of vicinal hydroxyl and methyl groups as well as di and tri-substituted double bonds in one single operation. In this review, we will highlight stereoselective protocols that have been used in natural product synthesis a...
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 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...
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ژورنال
عنوان ژورنال: Organic Letters
سال: 2005
ISSN: 1523-7060,1523-7052
DOI: 10.1021/ol052301p