201221-74-1Relevant academic research and scientific papers
Iodo Meyer-Schuster rearrangement of 3-alkoxy-2-yn-1-ols for β-mono (exclusively Z-selective)-/disubstituted α-iodo-α,β-unsaturated esters
Puri, Surendra,Thirupathi, Nuligonda,Reddy, Maddi Sridhar
, p. 5246 - 5249 (2015/02/19)
We herein present the iodo Meyer-Schuster rearrangement of 3-alkoxypropargyl alcohols for α-iodo-α,β-unsaturated esters using iodine or NIS in dichloromethane at ambient temperature. Substrates prepared from both aldehydes and ketones are found to be equally good feedstock for the reaction to produce β-mono-and-disubstituted products. Irrespective of the substitution, substrates prepared from aldehydes gave Z-isomers exclusively. (Chemical Equation Presented).
Titanium mediated olefination of aldehydes with α-haloacetates: An exceptionally stereoselective and general approach to (Z)-α-haloacrylates
Augustine, John Kallikat,Bombrun, Agnes,Venkatachaliah, Srinivasa,Jothi, Anandh
, p. 8065 - 8072 (2013/12/04)
An exceptionally stereoselective and general synthesis of (Z)-α-haloacrylates, ready to undergo various synthetic transformations, has been demonstrated from α-haloacetates and aldehydes in a one-pot manner via the titanium-enolate based asymmetric aldol
Synthesis of angularly fused aromatic compounds from alkenyl enediynes by a tandem radical cyclization process
Roy, Snigdha,Anoop, Anakuthil,Biradha, Kumar,Basak, Amit
supporting information; scheme or table, p. 8316 - 8319 (2011/10/09)
Let's get radical: A general synthetic route toward angularly ortho-fused polyaromatic [4]helicenes starting from aryl alkenyl N-substituted cyclic enediynes is described (see scheme; DMSO=dimethyl sulfoxide, Ns=4-nitrobenzenesulfonyl). The process involved a Bergman cyclization (BC) as the key step of an unprecedented tandem radical reaction.
One-pot approach to the conversion of alcohols into α-Iodoα, β-unsaturated Esters
Karama, Usama
experimental part, p. 3447 - 3451 (2011/01/12)
(Carboethoxymethylene)triphenylphosphorane 1 can undergo the tandem reaction of iodination-oxidation-Wittig reaction with alcohol in the presence of N-iodosuccinimide (NIS) and manganese dioxide. The reaction constitutes a stereoselective one-pot procedure for the preparation of Z-configured α-iodo-α,β-unsaturated esters in good to excellent yield. Copyright Taylor & Francis Group, LLC.
A facile one-pot synthesis of α-iodo-α,β-unsaturated esters
Zhang, Xingguo,Zhong, Ping,Chen, Fan
, p. 1729 - 1736 (2007/10/03)
Aldehydes reacted with (ethoxycarbonyliodomethyl)triphenylphosphonium iodide, tetrabutylammonium bromide, and potassium carbonate in methanol at 40°C to give α-iodo-α,β-unsaturated esters in good to excellent yield.
The stereospecific trifluoromethylation of α-iodo-α,β-unsaturated esters: A novel synthesis of (Z)-α-trifluoromethyl-α,β-unsaturated esters
Zhang, Xingguo,Qing, Feng-Ling,Peng, Yiyuan
, p. 79 - 82 (2007/10/03)
This paper describes simple and successful methods for the preparation of α-iodo-α,β-unsaturated esters. The trifluoromethylation of (Z)-α-iodo-α,β-unsaturated esters stereo-selectively provides (Z)-α-trifluoromethyl-α,β-unsaturated esters.
Synthesis of Imidazoles from Alkenes
Casey, Michael,Moody, Christopher J.,Rees, Charles W.
, p. 1933 - 1941 (2007/10/02)
Alkenes are converted into imidazoles through their epoxides by a sequence involving ring-opening with readily available 2-tributylstannyltetrazoles (8), dehydration of the resulting alcohols (9) using methyltriphenoxyphosphonium iodide in a improved procedure to give 1-alkenyltetrazoles (12), which give imidazoles (17) on photolysis.
