107408-34-4Relevant academic research and scientific papers
Comparative study of the N-isobutyl-(2E,6Z)-dodecadienamide chemical and electrochemical syntheses
Palma, Agustin,Cardenas, Jorge,Frontana-Uribe, Bernardo A.
experimental part, p. 283 - 293 (2010/04/22)
In order to show the advantages and limitations of organic electrosynthesis in the total synthesis of a natural product, one of the promising green chemistry techniques in organic chemistry, the synthesis of N-isobutyl-(2E,6Z)- dodecadienamide (3) was undertaken. Chemical and electrochemical routes that use the same intermediates were used to carry out the syntheses. Four reactions were compared from a green chemistry point of view in the synthesis of 3: (a) alcohol to aldehyde oxidation, (b) the Horner-Emmons reaction, (c) carboxylic acid amidation with triphenylphosphonium ions and (d) the Wittig reaction. All the electrolyses were carried out in non-divided cells at a constant current. The electrochemical method in the oxidation reaction of alcohols and the carboxylic acid amidation gave better yields (95% and 67%, respectively) than the corresponding chemical reactions. The Horner-Emmons reaction gave the same yields in both techniques (80-85%); however, the electrochemical method was more environmentally friendly, due to the fact that the base used was electrogenerated, avoiding corrosive and sensitive base manipulation. Finally, the electrochemical Wittig reaction was unsuccessful in the different experimental conditions attempted, and only the chemical method produced the target product. This study demonstrated that organic electrochemistry can be a reliable method for the synthesis of important intermediates, but not all electrochemical reactions can compete with the already well-established methods of organic chemistry.
Asymmetric synthesis of cyclic β-amino acids
O'Brien,Porter,Smith
, p. 1336 - 1338 (2007/10/03)
A convenient synthesis of cyclic β-amino acid derivatives (5-, 6- and 7-rings) is achieved via a four step sequence: (i) stereoselective Michael addition of substituted α-methylbenzylamines to α,β-unsaturated chloroesters; (ii) CAN-mediated deprotection; (iii) cyclisation and (iv) α-chloroethyl chloroformate-mediated α-methylbenzylamine deprotection.
Chiral alcohol-induced diastereoselective conjugate addition and cyclization
Fang, Chenglin,Suemune, Hiroshi,Sakai, Kiyoshi
, p. 4751 - 4754 (2007/10/02)
Conjugate addition of organocuprate reagents to α,β-unsaturated esters of chiral trans-cyclohexanediol proceeded diastereoselectively, and the intramolecular trapping of the generated enolate also afforded asymmetric cyclization products.
Lithium-Halogen Exchange-Initiated Cyclization Reactions. 3. Intramolecular Conjugate Addition Reactions of Unsaturated Acylphosphoranes
Cooke, Manning P.,Widener, Rexford K.
, p. 1382 - 1396 (2007/10/02)
The lithium-halogen exchange-initiated intramolecular conjugate addition reactions of some model unsaturated acylphosphoranes have been examined.The effects of halide type, chain length, and acceptor substitution pattern on the feasibility of ring construction were studied.The lithium-bromine exchange reactions in two 2-bromooaryl acceptors were found to be too slow, relative to competing side reactions, to allow practical carbocycle syntheses while 3-,4-,5-, and 6-membered carbocycles are formed in good to excellent yields from precursors that are vinyl and saturated primary iodides.Highly efficient intramolecular conjugate addition reactions to β,β-disubstituted acceptor units are possible, and intermediate anions from intramolecular conjugate addition reactions are readily captured with electrophiles.
A SHORT AND NOVEL SYNTHESIS OF THE PYRROLIZIDINE ALKALOIDS, (+/-)-SUPINIDINE AND (+/-)-TRACHELANTHAMIDINE
Kametani, Tetsuji,Higashiyama, Kimio,Otomasu, Hirotaka,Honda, Toshio
, p. 729 - 731 (2007/10/02)
The effective and short syntheses of the pyrrolizidine alkaloids, (+/-)-trachelanthamidine (8) and (+/-)-supinidine (12) were described.
