ChemInform Abstract: Horner—Emmons Reaction in the Synthesis of Esters of Unsaturated Acids from Adamantane Series and Related Carcass Compounds.

Abstract

2000 bridged compounds bridged compounds Q 0060 10 -095 Horner-Emmons Reaction in the Synthesis of Esters of Unsaturated Acids from Adamantane Series and Related Carcass Compounds. -Horner-Emmons reaction proves to be in principle suitable for the preparation of esters of unsaturated C-2 to C-3 carboxylic acids [cf. (III), (V)] containing bulky carcass substituents at the multiple bond. -(MIRYAN, N. I.; ISAEV, S. D.; KOVALEVA, S. A.; PETUKH, N. V.; DVORNIKOVA, E. V.; KARDAKOVA, E. V.; YURCHENKO, A. G.; Russ.

Copper‐Catalyzed Stereoselective Hydroarylation of 3‐Aryl‐2‐ propynenitriles with Arylboronic Acids

“…[10] Therefore, we used diethyl cyanomethylphosphonate as a less toxic nitrile precursor. According to a previous report, [11] pmethoxy-, 3,4-dimethoxy-, and 3,5-dimethoxy-substituted benzaldehydes were treated with an iodinated Horner-Emmons reagent in situ prepared from cyanomethylphosphonate in THF to yield 2-iodoacrylonitriles 2a-c in 82%, 76%, and 72% yields, respectively. Then, 2a was dehydroiodinated using 2 equivalents of lithium hexamethyldisilazide (LHMDS) in THF at À50 8C to obtain the desired alkyne 1a in 87% yield.…”

Synthesis of 3‐Arylindole‐2‐carboxylates via Copper‐Catalyzed Hydroarylation of o‐Nitrophenyl‐Substituted Alkynoates and Subsequent Cadogan Cyclization

“…According to the literature,11 commercially available o ‐nitrobenzaldehydes 2a – c were subjected to the Horner–Wadsworth–Emmons reaction with in‐situ prepared iodophosphonoacetate 1 , and the produced iodoacrylate intermediates were treated with NaH in the same flask. This one‐pot procedure afforded alkynoates 3a – c in 50–72% yields (Scheme ).…”

Synthesis of N,N′-Unsymmetrical 9-Amino-5,7-dimethyl-bispidines

“…It should also be stressed that this approach focuses on the modification of only two reaction centers, nitrogen atoms N3 and N7, while the carbon atom C9, potentially capable of acting as the third center of framework functionalization, is in their shadow. Only very few examples are described in the literature in which the carbonyl group is modified with the attachment of a new carbon chain to the C9 atom, for example, in the Horner–Wadsworth–Emmons reaction. − At the same time, a tendency to a decrease in the yield of this reaction is clearly observed with an increase in the number of substituents at the C1 and C5 atoms, that is, with an increase in steric hindrances near the C9 atom. In 1,5-disubstituted bispidines, the carbonyl group can be converted into an oxime, amino group, or hydroxyl group .…”