A Catalytic Asymmetric Vinylogous Mukaiyama Aldol Reaction
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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 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 کاملA One-Pot Tandem Strategy in Catalytic Asymmetric Vinylogous Aldol Reaction of Homoallylic Alcohols.
Reported is a rationally-designed one-pot sequential strategy that allows homoallylic alcohols to be employed in a catalytic, asymmetric, direct vinylogous aldol reaction with a series of activated acyclic ketones, including trifluoromethyl ketones, γ-ketoesters, and α-keto phosphonates, in high yields (up to 95%) with excellent regio- and enantio-selectivity (up to 99% ee). This modular combin...
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 tandem non-aldol aldol Mukaiyama aldol reaction.
[reaction: see text] A new one-pot tandem aldol process is described in which a secondary epoxy silyl ether is converted into the 1,5-bis-silyloxy-3-alkanone in good yield. Thus, treatment of the epoxy silyl ether 8 with TBSOTf and base affords the silyl enol ether 9 via non-aldol aldol rearrangement and addition of benzaldehyde and TBSOTf gives the ketone 10 with 4:1 syn selectivity. The diast...
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ژورنال
عنوان ژورنال: Organic Letters
سال: 2007
ISSN: 1523-7060,1523-7052
DOI: 10.1021/ol701851f