783-86-8Relevant academic research and scientific papers
Enantioselective intramolecular cyclopropanation of N-allylic-and N-homoallylic diazoacetamides catalyzed by chiral dirhodium(II) catalysts
Doyle, Michael P.,Eismont, Michail Y.,Protopopova, Marina N.,Kwan, Michelle M. Y.
, p. 1665 - 1674 (1994)
Diazodecomposition of N-(tert-butyl)-N-(3-buten-1-yl)diazoacetamides catalyzed by dirhodium(II) tetrakis[methyl 2-pyrrolidone-5(S)-carboxylate], Rh2(5S-MEPY)4, and tetrakis[methyl 2-oxazolidinone-4(S)-carboxylate], Rh2(4S-
A detailed investigation of the aza-prins reaction
Dobbs, Adrian P.,Guesne, Sebastien J. J.,Parker, Robert J.,Skidmore, John,Stephenson, Richard A.,Hursthouse, Mike B.
supporting information; experimental part, p. 1064 - 1080 (2010/06/13)
The development of a Lewis acid-promoted aza-Prins reaction to form piperidines and pyrrolidines is described. Indium trichloride has been found to be a highly successful and mild Lewis acid for promoting this reaction. A thorough mechanistic investigation is described, including the factors that influence the formation of the 5- or 6-membered ring product(s). The Royal Society of Chemistry.
Copper(I)-Mediated Synthesis of cis-Isoprenoids. Models for Natural Rubber
Parr, William J. E.
, p. 4101 - 4130 (2007/10/02)
Two copper(I)-mediated routes for the preparation of all-cis-2,6,10-trimethyl-2,6,10-dodecatriene are investigated.Reaction of the Grignard reagent derived from 1-bromo-4-methylpent-3-ene with CuBr, and then with excess propyne, gave a vinylcopper intermediate which could be alkylated with 1-iodo-3-methylpent-3-ene, to afford the required triene stereospecifically cis- in 28percent yield.Iodination of the same intermediate and subsequent conversion to 1-bromo-4,8-dimethyl-3,7-nonadiene is shown to occur with retention of configuration, so allowing the iterative construction of cis-isoprenoids.This vinylcopper-based route is shown to be also applicable to the synthesis of larger cis-isoprenoids.In contrast, the CuI-modified coupling reaction of the Grignard reagent from 1-chloro-2-methylbut-2-ene with neryl chloride gave a mixture of triene isomers.
