941304-01-4Relevant 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 (2014)
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).
Lewis acid-catalyzed Meyer-Schuster reactions: methodology for the olefination of aldehydes and ketones
Engel, Douglas A.,Lopez, Susana S.,Dudley, Gregory B.
, p. 6988 - 6996 (2008/09/21)
In principle, the most efficient and atom-economical means of converting an aldehyde or ketone into the homologated α,β-unsaturated ester is through addition/rearrangement sequences involving acetylenic π-bonds (Scheme 1). Implementation of such a strategy for the synthesis of α,β-unsaturated esters is presented: addition of ethoxyacetylene followed by scandium(III) triflate-catalyzed Meyer-Schuster rearrangement reaction. Stereoselectivities range from good to excellent in the formation of disubstituted α,β-unsaturated esters from aldehydes (Table 3). The two-stage olefination of even the most hindered ketones proceeds with near perfect efficiency (Table 4).
The Meyer-Schuster rearrangement of ethoxyalkynyl carbinols
Lopez, Susana S.,Engel, Douglas A.,Dudley, Gregory B.
, p. 949 - 953 (2008/02/02)
The combination of electron-rich alkoxyacetylenes and cationic gold catalysts provides excellent reactivity for the Meyer-Schuster rearrangement under mild conditions. Optimization of the reaction conditions with respect to stereoselectivity and investigations into the scope and mechanism of the rearrangement of secondary ethoxyalkynyl carbinols (γ-ethoxy-substituted propargyl alcohols) to α,β-unsaturated esters are described. Georg Thieme Verlag Stuttgart.
Virtually complete E-selective α,β-unsaturated ester synthesis by Hg(OTf)2-catalyzed hydration of sec-ethoxyalkynyl acetate
Nishizawa, Mugio,Hirakawa, Hiroko,Nakagawa, Yuki,Yamamoto, Hirofumi,Namba, Kosuke,Imagawa, Hiroshi
, p. 5577 - 5580 (2008/09/17)
The reaction of alkyl-substituted sec-ethoxyalkynyl acetates with water catalyzed by Hg(OTf)2 afforded α,β-unsaturated esters in excellent yield with high catalytic turnover up to 1000 times under very mild reaction conditions with virtually complete E-selectivity, superior even to that of the HWE reaction.
