Journal ArticleDOI
NEW CROSS-ALDOL REACTION Via VINYLOXYBORANES
Teruaki Mukaiyama,Tan Inoue +1 more
TLDR
In this paper, a new synthesis of cross-aldols from two different carbonyl compounds by using di-n-butylboryl trifluoromethanesulfonate and tertiary amine is described.Abstract:
A new synthesis of cross-aldols from two different carbonyl compounds by using di-n-butylboryl trifluoromethanesulfonate and tertiary amine is described In the case of methyl ketones, the reaction takes place in regiospecific manner to afford the corresponding aldols in good yieldsread more
Citations
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Journal ArticleDOI
Modern aldol methods for the total synthesis of polyketides.
Bernd Schetter,Rainer Mahrwald +1 more
TL;DR: This Review illustrates by means of selected syntheses of natural products the new variants of the aldol addition, which includes a Aldol additions with various metal enolates, as well as metal-complex-catalyzed, organocatalytic, and biocatalysis methods.
Journal ArticleDOI
The Mukaiyama aldol reaction: 40 years of continuous development.
TL;DR: A directed cross-aldol reaction of silyl enol ethers with carbonyl compounds, such as aldehydes and ketones, promoted by a Lewis acid, a reaction which is now widely known as the Mukaiyama aldol reaction was first reported in 1973, and this year marks the 40th anniversary.
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
Scandium trifluoromethanesulfonate (Sc(OTf)3). A novel reusable catalyst in the Diels-Alder reaction
TL;DR: Scandium trifluoromethanesulfonate (Sc(OTf)3) was used as a Lewis acid catalyst in the Diels-Alder reaction.
Journal ArticleDOI
Enantioselective total synthesis of altohyrtin c (spongistatin 2)
David A. Evans,B. Wesley Trotter,Paul J. Coleman,Cote Bernard,Luiz C. Dias,Hemaka A. Rajapakse,Andrew N. Tyler +6 more
TL;DR: The first total synthesis of a spongipyran macrolide, altohyrtin C, was described in this paper, which relies on a regioselective macrolactonization, a stere-lective Wittig coupling of the two major synthetic fragments, a complex anti-aldol reaction to join the C1-C15 and C16-C28 spiroketal regions, and an anomeric sulfone acylation to join C29-C37 and C38-C43 pyran regions.
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
Chemistry of carbanions. XXIII. Use of metal complexes to control the aldol condensation
Journal ArticleDOI
Directed Aldol Condensations
G. Wittig,H. Reiff +1 more
TL;DR: In this article, a new procedure for aldol condensations for the preparation of α,β-unsaturated carbonyl compounds was described, using metalated Schiff's bases as ambident anions.
Journal ArticleDOI
The reaction of trialkylboranes with diazoacetone. A new ketone synthesis
John Hooz,Siegfried Linke +1 more
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Regio- and stereoselective cross-aldol reactions via dialkylboryl triflates.
Tan Inoue,Teruaki Mukaiyama +1 more