Effective Synthesis of 5-Substituted Butenolide Derivatives by Using Cinchonidine-derived Quaternary Ammonium Phenoxide Catalyst

Nagao, Hitoshi; Yamane, Yoshinobu; Mukaiyama, Teruaki

doi:10.1246/cl.2007.8

Cited by 55 publications

(24 citation statements)

References 11 publications

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“…[67] The reaction wass tudied at first with benzaldehydea nd 2-(trimethylsilyloxy)furani nt he presence of 10 mol %o ft he chiral salt. Therefore, Mukaiyama's group reported an organocatalytic vinylogous aldol reactionb etween silyloxyfurans 123 and aldehydes 16 under chiral ammonium salt catalysis 124 (Scheme 43).…”

Section: Ammonium Salt Catalystsmentioning

confidence: 99%

Development and Application of Asymmetric Organocatalytic Mukaiyama and Vinylogous Mukaiyama‐Type Reactions

Frías

Cieślik

Fraile

et al. 2018

Chemistry A European J

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Organocatalysis is a growing area that is benefiting from advances in many fields. Its implementation has begun in areas such as supramolecular chemistry, organic chemistry and natural product synthesis. While a considerable number of important publications in the field of organocatalytic Mukaiyama-type additions have been reported, they are yet to be fully covered in a review. Therefore, we would like to highlight the applications of various kinds of organocatalysts in Mukaiyama-type reactions, while also including the vinylogous Mukaiyama variation. Herein we describe and discuss the development and current state of the art of the organocatalytic Mukaiyama reaction, vinylogous Mukaiyama and related reactions.

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Section: Ammonium Salt Catalystsmentioning

confidence: 99%

Development and Application of Asymmetric Organocatalytic Mukaiyama and Vinylogous Mukaiyama‐Type Reactions

Frías

Cieślik

Fraile

et al. 2018

Chemistry A European J

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“…Indeed, one could consider to associate the phenoxide anion with a chiral quaternary ammonium cation through a chiral quaternary ammonium phenoxide ion pair organocatalyst. Such a type of catalyst, even if already described in the literature mainly by the group of Mukaiyama in 2000′s, were then sparingly exploited in the literature. [21],[22] We thus decided to undertake the synthesis of such catalysts and to assess their performances in enantioselective protonation of silyl enol ethers 2 derived from cyclic aromatic ketones (Scheme ) …”

Section: From Acyl Transfer To Enantioselective Protonationmentioning

confidence: 99%

“…From a mechanistic point of view, one could envision the formation of the trimethylsilyloxyfuranone (TMSOF) as a key intermediate followed a Muakaiyama‐aldol type pathway . To preclude this assumption, a control experiment was achieved in the presence of a preformed TMSOF and the same preformed chiral ammonium aryloxide QN + 4,4‐MeOC 6 H 4 O − .…”

Section: Protonation or Deprotonation: That Is The Question?mentioning

confidence: 99%

New Developments in Chiral Cooperative Ion Pairing Organocatalysis by Means of Ammonium Oxyanions and Fluorides: From Protonation to Deprotonation Reactions.

2016

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This personal account summarizes our contribution to the ion pairing organocatalysis mainly by use of chiral quaternary or tertiary ammonium fluorides, aryloxides and carboxylates. Starting from an experimental observation, we were able to develop several approaches for the enantioselective protonation of silyl enolates and enol esters giving rise to chiral carbonyl compounds bearing a stereogenic center at the α-position. Moving from protonation to deprotonation reactions, chiral ammonium ion pair catalysts were successfully applied to several asymmetric transformations such as an Henry reaction or a direct vinylogous aldol reaction to cite a few. An outlook of further possible developments in this field of research will also be discussed.

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“…The vinylogous Mukaiyama aldol reaction rapidly provides 5-[hydroxy(aryl) methyl]furan-2(5H)-ones by addition of the g carbon of a dienolate onto a carbonyl framework (for a review, see [120]). Over the past few years, some elegant enantioselective versions of this reaction using catalytic amounts of various chiral mediators have been described (for a review on enantioselective vinylogous Mukaiyama aldol, see [121]) [122][123][124][125], including a recent organocatalytic approach [126]. Recently, synthetic methods involving numerous lanthanide triflates have been reported [72,[127][128][129].…”

Section: Bismuth-catalyzed Mukaiyama Aldol Reactionmentioning

confidence: 99%

Bismuth-Catalyzed Addition of Silyl Nucleophiles to Carbonyl Compounds and Imines

Ollevier

2011

Bismuth-Mediated Organic Reactions

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Bismuth triflate was found to be an efficient catalyst both in the Mannich-type reaction of silyl enolates and in the Sakurai reaction of allyltrimethylsilane with N-alkoxycarbonylamino sulfones. The reactions proceeded smoothly with a low catalyst loading of Bi(OTf)(3)·4H(2)O (0.5-5.0 mol%) to afford the corresponding protected β-amino carbonyl compounds and homoallylic amines in very good yields (up to 96%). The latter compounds could also be obtained via a bismuth-mediated three-component reaction. We have also developed an efficient vinylogous Mukaiyama aldol reaction of 2-(trimethylsilyloxy)furan with various aromatic aldehydes mediated by bismuth triflate in a low catalyst loading (1 mol%). The reaction proceeds rapidly and affords the corresponding 5-[hydroxy(aryl)methyl]furan-2(5H)-ones in high yields with good to very good diastereoselectivities (diastereoisomeric ratios>98:2). Such selectivities, although previously reported with other Lewis acids, could be achieved with a much lower catalyst loading. 5-[Hydroxy(alkyl)methyl]furan-2(5H)-ones derived from ketones could also be obtained with good diastereoselectivities. The vinylogous Mukaiyama aldol reaction has also been extended to 2,2-dimethyl-6-methylene-4-(trimethyl-silyloxy)-1,3-diox-4-ene using 1 mol% of Bi(OTf)(3)·4H(2)O.

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Effective Synthesis of 5-Substituted Butenolide Derivatives by Using Cinchonidine-derived Quaternary Ammonium Phenoxide Catalyst

Cited by 55 publications

References 11 publications

Development and Application of Asymmetric Organocatalytic Mukaiyama and Vinylogous Mukaiyama‐Type Reactions

Development and Application of Asymmetric Organocatalytic Mukaiyama and Vinylogous Mukaiyama‐Type Reactions

New Developments in Chiral Cooperative Ion Pairing Organocatalysis by Means of Ammonium Oxyanions and Fluorides: From Protonation to Deprotonation Reactions.

Bismuth-Catalyzed Addition of Silyl Nucleophiles to Carbonyl Compounds and Imines

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