- The reaction of α,β-acetylenic ketones with dicyclohexylborane: Stereoselective synthesis of functionalized trisubstituted olefins
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Allenoxyborinates, easily generated via the 1,4-addition of dicyclohexylborane to α,β-acetylenic ketones, react in situ with excess starting ketone to afford stereodefined, functionalized trisubstituted olefins in high yields.
- Kabalka, George W.,Yu, Su,Li, Nan-Sheng,Lipprandt, Ute
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Read Online
- De Novo Asymmetric Synthesis of Phoracantholide J
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A de novo asymmetric total synthesis of the macrolide natural product (S)-phoracantholide J has been achieved in 10 steps from the commodity chemicals (1-pentyne, ethyl acrylate, acetaldehyde, and hydrogen). The asymmetry of the route was introduced by a Noyori reduction of a 3-yn-2-one, which makes the route equally amenable to the synthesis of either enantiomer. In addition, this route relies upon an alkyne zipper, a hydroalkynylation, and a macrolactonization to complete the synthesis.
- Avocetien, Kenneth F.,Li, Jiazhen J.,Liu, Xiaofan,Wang, Yanping,Xing, Yalan,O'Doherty, George A.
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supporting information
p. 4970 - 4973
(2016/10/14)
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- The Autoxidation of Hept-3-yne
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In the reaction mixtures of the oxidation of hept-3-yne with molecular oxygen as products of the attack on the C-C triple bond heptane-3,4-dione, propionic and butyric acids and a very small amount of 2-ethylvaleric acid were found.Hept-2-en-4-one and hept-3-en-5-one were probably present, but could not be identified unambiguously.As in the case of the isomeric octynes the main primary reaction products were the hydroperoxides formed by attack on the C-H bonds in α-position to the CC triple bond.
- Brose, Th.,Pritzkow, W.,Sebald, F.,Voerckel, V.
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p. 951 - 956
(2007/10/02)
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- Synthesis of (R)-(-)-10-Methyl-2-tridecanone, the Pheromone of the Southern Corn Rootworm
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(R)-(-)-10-Methyl-2-tridecanone, the pheromone of Diabrotica undecimpunctata howardi Barber, was synthesized from (R)-(+)-citronellyl acetate.
- Senda, Shuji,Mori, Kenji
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p. 795 - 798
(2007/10/02)
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- Z/E-Isomerization of Unsaturated Carboxylic Acids during the Kolbe Electrolysis
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Z-4-Enoic acids partially isomerize to E-configurated products in the Kolbe electrolysis.The results from methyl and deuterium labelled carboxylic acids 2 and 16 support an isomerization via a reversible ring closure to cyclopropylcarbinyl radicals.The double bonds of Z-N-enoic acids with N>/= 5 fully retain their configuration in the Kolbe electrolysis; for N=6,7 cyclic products are formed to some extent, which is in accord with the reactivity of 5- and 6-alkenyl radicals.
- Huhtasaari, Matti,Schaefer, Hans J.,Luftmann, Heinrich
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p. 537 - 548
(2007/10/02)
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