201735-42-4Relevant academic research and scientific papers
New allene synthesis via carbocupration - Zinc carbenoid homologation and β-elimination sequence
Varghese, Jos P.,Knochel, Paul,Marek, Ilan
, p. 2849 - 2852 (2000)
Polysubstituted propadienes are obtained in good to excellent yields by the consecutive carbocupration - homologation - β-elimination reactions on the easily accessible alkynyl sulfoxides or sulfones. This one-pot reaction also allows the preparation of f
Studies on Cu(I)-catalyzed synthesis of simple 3-substituted 1,2-allenes and optically active 2-substituted secondary 2,3-allenols
Li, Jing,Zhou, Chao,Fu, Chunling,Ma, Shengming
experimental part, p. 3695 - 3703 (2009/09/05)
The sequential treatment of terminal alkynes or propargylic alcohols with n-BuLi and MOMCl afforded the corresponding propargylic methyl ethers, which would react with primary alkyl Grignard reagents under the catalysis of CuBr to afford 3-substituted 1,2-allenes or 2-substituted secondary 2,3-allenols, respectively. The reaction may be applied to the synthesis of optically active 2-substituted secondary 2,3-allenols with up to >99% ee without any protection to the free hydroxyl group in the starting 4-hydroxy-2-alkynyl methyl ethers.
Carbocupration/zinc carbenoid homologation and β-elimination reactions for a new synthesis of allenes - Application to the enantioselective synthesis of chiral allenes by deracemization of sp3-organometallic derivatives
Varghese, Jos P.,Zouev, Irena,Aufauvre, Lionel,Knochel, Paul,Marek, Ilan
, p. 4151 - 4158 (2007/10/03)
A new and straightforward carbocupration/zinc homologation/β-elimination reaction sequence allows the one-pot synthesis of polysubstituted allenes from acetylenic sulfoxides in excellent isolated chemical yields. Secondary zinc carbenoids were used for the homologation reaction, and so a new synthesis of 1,1-diiodoalkanes is described. This methodology also allows the synthesis of chiral allenes through thermodynamic equilibration of secondary organometallic derivatives. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002.
Manganese-catalyzed phenylation of acetylenic compounds with a phenyl grignard reagent
Yorimitsu, Hideki,Tang, Jun,Okada, Kenji,Shinokubo, Hiroshi,Oshima, Koichiro
, p. 11 - 12 (2007/10/03)
Treatment of homopropargylic alcohol derivatives or phenylacetylene compounds with phenylmagnesium bromide in the presence of a catalytic amount of manganese(II) chloride afforded phenylated products in good yields with high regio-and stereoselectivities.
