- β-LACTONE AS INTERMEDIATE IN THE PERKIN REACTION CATALYZED BY TERTIARY AMINES
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The Perkin reaction catalyzed by tertiary amines is found to run not according to the aldol-type condensation mechanism but according to the mechanism in which the first stage is the formation and cycloaddition of ketene, yielding a β-lactone, which cleaves to the unsaturated acid.
- Kinastowski, Stefan,Nowacki, Antoni
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Read Online
- Direct acylation of carrier proteins with functionalized β-lactones
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As the key component of many biosynthetic assemblies, acyl-carrier proteins offer a robust entry point for introduction of small molecule probes and pathway intermediates. Current labeling strategies primarily rely on modifications to the phosphopantethei
- Amoroso, Jon W.,Borketey, Lawrence S.,Prasad, Gitanjeli,Schnarr, Nathan A.
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supporting information; experimental part
p. 2330 - 2333
(2010/10/03)
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- A one-pot synthesis of 3-arylglutaric anhydrides by reaction of ketene with aromatic aldehydes and ketones
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Aromatic aldehydes and ketones react with ketene under Lewis acid catalysis to produce β-lactones, which in situ react with another molecule of ketene to produce 3-arylglutaric anhydrides. The mechanism, scope, and limitation of this one-pot synthesis of 3-substituted glutaric anhydrides are discussed.
- Matsunaga, Hirokazu,Ikeda, Kiyoshi,Iwamoto, Ken-ichi,Suzuki, Yumiko,Sato, Masayuki
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experimental part
p. 2334 - 2336
(2009/09/06)
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- Studies of the asymmetric [2+2] cycloaddition of silylketenes and aldehydes employing Ti-TADDOL catalysts
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Ti-TADDOL catalysts provide good reactivity and moderate enantioselectivity in the asymmetric [2+2] cycloaddition of silyl ketenes and aldehydes. The effects of potential bidentate chelation of benzyloxy substituted aldehydes and of the steric size of the ketene silyl group were studied.
- Yang, Hong Woon,Romo, Daniel
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p. 2877 - 2880
(2007/10/03)
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- GENERATION AND PROPERTIES OF ACETIC ANHYDRIDE CARBANION
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In the reaction between ketene and acetate ions the labile acetic anhydride carbanion is formed.This carbanion generated in situ in the presence of 4-nitrobenzaldehyde undergoes cycloaddition yielding β-lactone and, further, 4-nitrocinnamic acid (Path A).It can also undergo numerous inter- and intramolecular reactions producing various by-products, i.e.CO2, acetoacetic acid (tetrabutylammonium salt), propen-2-ol acetate, acetone, acetylacetone (Path B).Analogical products were obtained with carbanion generated from acetic anhydride by sodium hydride.
- Kinastowski, Stefan,Kasprzyk, Henryk,Nowacki, Antoni
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p. 771 - 776
(2007/10/02)
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