Erythro-selective aldol reaction via tris(dialkylamino)sulfonium enolates

Noyori, Ryoji; Nishida, Ikuo; Sakata, J.

doi:10.1021/ja00398a047

Cited by 167 publications

(38 citation statements)

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“…Ring-opening fluorination of oxiranes is readily carried out with TBA · H 2 F 3 [ 180]. TASF (Et) generates a fluoride ion under strictly anhydrous conditions and thus is used for an aldol reaction of enol silyl ethers with aldehydes [182,183]. The coproduced reagent TBA · HF2 is assumed to be readily converted back to TBA·H 2 F 3 by KHF 2 • Thus, TBA·H 2 F 3 is considered to be a highly nucelophilic fluoride ion supplier.…”

Section: Tfoi)~jomentioning

confidence: 99%

Organofluorine Compounds

Hiyama¹

2000

969

318

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Section: Tfoi)~jomentioning

confidence: 99%

Organofluorine Compounds

Hiyama¹

2000

969

318

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“…(35)] (5g, 18). Noyori and co-workers have also investigated the use of tris(diethylamino)sulfonium (TAS + ) difluorotrimethylsiliconate (55) as a catalyst for the reaction of enolsilanes with aldehydes (8). Although it has been proposed (18,55) that this reaction involves a tetraalkylammonium enolate, the possibility of a pentacoordinated siliconate ion (42) has not been discounted.…”

Section: Enolsilanes and Enolstannanesmentioning

confidence: 99%

The Aldol Addition Reaction

Heathcock

1984

Asymmetric Synthesis

244

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“…The existence of free enolate anions under these reaction conditions has been demonstrated [30,31] and an extended-transition-state model has been proposed to account for the observed diastereoselectivity (Fig. 3.2) [32][33][34].…”

Section: Catalytic Aldol Additionsmentioning

confidence: 80%

Aldol Reactions

Schetter

Mahrwald

2005

Quaternary Stereocenters

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IntroductionThe aldol reaction and the related Claisen reaction are some of the most powerful methods for carbon-carbon bond formation [1]. Particularly since the mid-1980s, intensive research in this field has generated several new routes to stereo-and regiocontrol [2] as well as new catalytic reaction types. Although, overall, many variations of these reactions exist, only a few of them are generally applicable pathways for the creation of quaternary carbon centers.Formally, there exist two main reaction types to create a quaternary stereocenter via aldol additions (and related reactions). The first pathway is the addition of a carbonyl compound 1 (or a correspondding activated species) with two different -substituents (R 2 R 3 ) to another carbonyl compound 2. This method generates a quaternary carbon atom next to the carbonyl group of the aldols 3 and 4 (Scheme 3.1).The second pathway (Scheme 3.2) is the aldol addition of an enolizable carbonyl compound 5 to a carbonyl function 6 with two different substituents (R 2 R 3 ), which creates an aldol 7 with an asymmetric tertiary alcohol. Scheme 3.1 Scheme 3.2 Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis. Edited

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Erythro-selective aldol reaction via tris(dialkylamino)sulfonium enolates

Cited by 167 publications

References 0 publications

Organofluorine Compounds

Organofluorine Compounds

The Aldol Addition Reaction

Aldol Reactions

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