Catalytic Asymmetric Aldol Reaction of Silyl Enol Ethers with Aldehydes by the Use of Chiral Diamine Coordinated Tin(II) Triflate

Mukaiyama, Teruaki; Kobayashi, Shū; Uchiro, Hiromi; Shiina, Isamu

doi:10.1246/cl.1990.129

Cited by 89 publications

(28 citation statements)

References 4 publications

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“…It was postulated that the precursor 26 (Scheme 4) of the ring-closed product ( 1’ ) possessing a syn -α-methyl-β-hydroxy carboxylic acid moiety could be accessed via an asymmetric Mukaiyama aldol reaction [40–42] and our universal lactonization strategy. The synthetic route to 1’ is shown in Scheme 4.…”

Section: Resultsmentioning

confidence: 99%

Total synthesis of the proposed structure of astakolactin

Tonoi¹,

Mameda²,

Fujishiro³

et al. 2014

Beilstein J. Org. Chem.

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Section: Resultsmentioning

confidence: 99%

Total synthesis of the proposed structure of astakolactin

Tonoi¹,

Mameda²,

Fujishiro³

et al. 2014

Beilstein J. Org. Chem.

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“…Mukaiyama group gave important contribution in this context (177). In 1990s, Mukaiyama and Kobayashi group developed several highly enantioselective aldol reactions of silyl ethers with aldehydes that were catalyzed by the use of different chiral diamine coordinated tin(II) triflate (Sn(OTf) 2 ) (Scheme 44) (178)(179)(180)(181). Other groups have also found the combination of Sn(OTf) 2 and chiral organic base, such as (-)-sparteine, promoted the Mukaiyama aldol reaction smoothly with good enantioselectivities (182)(183)(184).…”

Section: Main Group Metals-base Catalystsmentioning

confidence: 99%

Aldol Reaction—Homogeneous

Cai

2011

Encyclopedia of Catalysis

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The aldol reaction is one of the oldest and important methods for the construction of carbon–carbon bonds in organic chemistry. Over the last 30 years, tremendous efforts have resulted in the development of many highly sophisticated and efficient catalytic methods of modern aldol reactions in catalytic chemo‐, regio‐, enantio‐, and diastereoselective manners. This review outlined those efforts in homogeneous catalysis and discussed with selected examples (331 publications) according to the different elemental types of catalysts, for example, transition metals and rare earth metals based Lewis acids, main group metals based catalysts, multifunctional catalysts, and metal‐free catalysts.

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“…(24)]. This resulted in the aldol product 53 being obtained in good yields and with high enantioselectivities 88. The selectivities are improved by using propionitrile as the solvent instead of dichloromethane because the rate of Sn–Si exchange is faster in propionitrile than in dichloromethane 89…”

Section: Crossed Aldol Reactions Via Boron and Silicon Enolate Intmentioning

confidence: 99%

Explorations into New Reaction Chemistry

Mukaiyama

2004

Angew Chem Int Ed

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191

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This Review describes the basic concepts that have guided our exploration of new chemical reactions by giving examples of results from my research group. Our strategy of carrying out research is to investigate three to four different topics at a time so we can gather as many results as possible. These may at first appear unrelated to each other but may have the potential to be united into a greater hypothesis after repeated feedback. Three scenarios from our research are presented: the "oxidative-reductive condensation reaction" devised in 1960, which after an interval of nearly 40 years brought forth the new concept of using compounds of structure Ph(2)POR as reducing reagents; the "TiCl(4)-aldol reaction" of 1973 that eventually led to the present "base-promoted aldol reaction" through a chain of ideas; and the "glycosylation reaction using fluorosugars" from 1984 which recently bloomed into "stereocontrolled glycosylation". Thus, it can be said that by reviewing what we had done before, we were able to expand on it to achieve new outcomes.

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Catalytic Asymmetric Aldol Reaction of Silyl Enol Ethers with Aldehydes by the Use of Chiral Diamine Coordinated Tin(II) Triflate

Abstract: Highly enantioselective aldol reaction of silyl enol ethers with aldehydes is performed by the use of a catalytic amount of chiral diamine coordinated tin(II) triflate according to a slow addition procedure.

Cited by 89 publications

References 4 publications

Total synthesis of the proposed structure of astakolactin

Total synthesis of the proposed structure of astakolactin

Aldol Reaction—Homogeneous

Explorations into New Reaction Chemistry

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