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Journal ArticleDOI

An efficient method for the preparation of threo cross-aldols from silyl enol ethers and aldehydes using trityl perchlorate as a catalyst

Teruaki Mukaiyama, +2 more
- 05 Apr 1985 - 
- Vol. 14, Iss: 4, pp 447-450
TLDR
In this article, three cross-aldol products are formed in good yields by treating tert-butyldimethylsilyl enol ethers with aldehydes in the presence of a catalytic amount of trityl perchlorate.
Abstract
Threo cross-aldol products are predominantly formed in good yields by treating tert-butyldimethylsilyl enol ethers with aldehydes in the presence of a catalytic amount of trityl perchlorate.

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Citations
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Journal ArticleDOI

Diastereoselection in lewis-Acid-mediated aldol additions.

TL;DR: The evolution of stereoselective Lewis-acid-mediated aldol-type addition up to the recent development of chiral Lewis acids is covered, which gives the main advantages in the Mukaiyama approach are the chemoselectivity of the reaction and the possibility of stereOSElective execution.
Journal ArticleDOI

Phosphonium Salt Organocatalysis

TL;DR: In this paper, the application of chiral phosphonium salts as Lewis acid catalysts for a variety of C, O and N bond-forming reactions under homogeneous conditions is discussed.
Journal ArticleDOI

Explorations into new reaction chemistry.

TL;DR: The basic concepts that have guided the exploration of new chemical reactions by giving examples of results from my research group are described, and it can be said that by reviewing what the authors had done before, they were able to expand on it to achieve new outcomes.
Journal ArticleDOI

Highly anti-selective asymmetric aldol reactions using chiral zirconium catalysts. Improvement of activities, structure of the novel zirconium complexes, and effect of a small amount of water for the preparation of the catalysts.

TL;DR: It has been shown that even aldol reactions of less reactive substrates proceeded smoothly using the novel zirconium catalysts, and NMR studies of these catalysts suggested that the catalyst would form a dimeric structure and that the water affected the catalyst formation.
References
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Journal ArticleDOI

New cross-aldol reactions. Reactions of silyl enol ethers with carbonyl compounds activated by titanium tetrachloride

TL;DR: Mukaiyama et al. as mentioned in this paper showed that with the addition of titanium tetrachloride, silyl enol ethers can react with either aldehydes or ketones forming crossed aldol products.
Journal ArticleDOI

Titanium Tetrachloride in Organic Synthesis [New synthetic methods (21)]

TL;DR: In this paper, the authors made mention of carbon-carbon linkage with TiCl4 which permits the synthesis of hydroxy ketones and carbonyl compounds of the Michael adduct type.
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